Production Method 1

1346132-35-1

87905-98-4

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0 °C; overnight
1.2 Reagents: Water

Reference

Asymmetric Organocatalytic Intramolecular Aza-Michael Addition of Enone Carbamates: Catalytic Enantioselective Access to Functionalized 2-Substituted Piperidines

Liu, Jian-Dong; et al, Advanced Synthesis & Catalysis, 2011, 353(14-15), 2721-2730

Production Method 2

2508-29-4

87905-98-4

Reaction Conditions

1.1 Reagents: Sodium carbonate Solvents: Dichloromethane ,  Water ;  4 h, rt

Reference

Analysis of the dispersity in carbohydrate loading of synthetic glycoproteins using MALDI-TOF mass spectrometry

Patel, Mitul K.; et al, Chemical Communications (Cambridge, 2010, 46(48), 9119-9121

Production Method 3

220645-58-9

1443018-38-9

87905-98-4

2227068-13-3

Reaction Conditions

1.1 Reagents: Tosyl chloride ,  Silver triflate Solvents: Dichloromethane ;  3 h, rt
1.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 4

87905-98-4

2227068-88-2

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dimethylformamide ,  Water ;  2 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt
2.1 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Catalysts: 4-(Dimethylamino)pyridine Solvents: Dimethylformamide ,  Dichloromethane ;  20 min, 90 °C
2.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 5

57224-63-2

87905-98-4

2227068-88-2

Reaction Conditions

1.1 Reagents: Imidazole Catalysts: 4-(Dimethylamino)pyridine Solvents: Dimethylformamide ;  7 h, 45 °C
2.1 Reagents: Sodium hydroxide Solvents: Dimethylformamide ,  Water ;  2 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  rt
3.1 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Catalysts: 4-(Dimethylamino)pyridine Solvents: Dimethylformamide ,  Dichloromethane ;  20 min, 90 °C
3.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 6

87905-98-4

Reaction Conditions

1.1 Reagents: Boron trifluoride etherate Solvents: Dichloromethane ;  0 °C; 2 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized, rt
2.1 Reagents: Sodium methoxide Solvents: Methanol ;  overnight, rt
2.2 Reagents: Amberlite IR 120 ;  rt
3.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; overnight, rt
3.2 Reagents: Water ;  0 °C
4.1 Reagents: N-Iodosuccinimide ,  Trifluoromethanesulfonic acid Solvents: Dichloromethane ;  2 - 3 h, -40 °C
4.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 7

2508-29-4

87905-98-4

Reaction Conditions

1.1 Reagents: Sodium bicarbonate Solvents: Tetrahydrofuran ,  Water ;  0 °C → rt; overnight, rt

Reference

Strategies for the Asymmetric Construction of Pelletierine and its Use in the Synthesis of Sedridine, Myrtine, and Lasubine

Zaidan, Raed K. ; et al, European Journal of Organic Chemistry, 2019, 2019(31-32), 5354-5367

Production Method 8

2508-29-4

87905-98-4

Reaction Conditions

1.1 Reagents: Sodium bicarbonate Solvents: Tetrahydrofuran ,  Water ;  0 °C; 0 °C → rt; 12 h, rt

Reference

Beyond Switches: Ratcheting a Particle Energetically Uphill with a Compartmentalized Molecular Machine

Chatterjee, Manashi N.; et al, Journal of the American Chemical Society, 2006, 128(12), 4058-4073

Production Method 9

1443018-38-9

87905-98-4

Reaction Conditions

1.1 Reagents: N-Iodosuccinimide ,  Trifluoromethanesulfonic acid ,  4-Methylphenyl 2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-β-D-g… Solvents: Dichloromethane ;  2 - 3 h, -40 °C
1.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 10

1927-62-4

87905-98-4

Reaction Conditions

1.1 Reagents: Triethylsilane ,  Hexamethyldisilazane Catalysts: Ferrous sulfate heptahydrate Solvents: Dichloromethane ;  24 h, rt

Reference

Iron-catalyzed four-component reaction for the synthesis of protected primary amines

Yang, Bai-ling; et al, European Journal of Organic Chemistry, 2007, (28), 4646-4650

Production Method 11

137160-76-0

2508-29-4

87905-98-4

Reaction Conditions

Reference

Synthesis of amides from carboxylic acids and derivatives

Ziegler, T., Science of Synthesis, 2005, 21, 43-75

Production Method 12

288580-32-5

87905-98-4

Reaction Conditions

1.1 Reagents: Triphenylphosphine ,  Water Solvents: Tetrahydrofuran ;  rt; 10 h, 40 °C
1.2 Reagents: Triethylamine
1.3 Reagents: Water
2.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0 °C; overnight
2.2 Reagents: Water

Reference

Asymmetric Organocatalytic Intramolecular Aza-Michael Addition of Enone Carbamates: Catalytic Enantioselective Access to Functionalized 2-Substituted Piperidines

Liu, Jian-Dong; et al, Advanced Synthesis & Catalysis, 2011, 353(14-15), 2721-2730

Production Method 13

121671-76-9

87905-98-4

Reaction Conditions

1.1 Reagents: Triethylamine ,  Methanesulfonyl chloride Solvents: Dichloromethane ;  10 min, 0 °C
1.2 Reagents: Sodium azide Solvents: Dimethylformamide ;  rt; overnight, 50 °C
2.1 Reagents: Triphenylphosphine ,  Water Solvents: Tetrahydrofuran ;  rt; 10 h, 40 °C
2.2 Reagents: Triethylamine
2.3 Reagents: Water
3.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0 °C; overnight
3.2 Reagents: Water

Reference

Asymmetric Organocatalytic Intramolecular Aza-Michael Addition of Enone Carbamates: Catalytic Enantioselective Access to Functionalized 2-Substituted Piperidines

Liu, Jian-Dong; et al, Advanced Synthesis & Catalysis, 2011, 353(14-15), 2721-2730

Production Method 14

2140187-93-3

1443018-38-9

87905-98-4

2227068-88-2

Reaction Conditions

1.1 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Catalysts: 4-(Dimethylamino)pyridine Solvents: Dimethylformamide ,  Dichloromethane ;  20 min, 90 °C
1.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 15

92954-90-0

1443018-38-9

87905-98-4

Reaction Conditions

1.1 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Catalysts: 4-(Dimethylamino)pyridine Solvents: Dimethylformamide ,  Dichloromethane ;  20 min, 90 °C
1.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 16

131531-76-5

1443018-38-9

87905-98-4

Reaction Conditions

1.1 Reagents: N-Iodosuccinimide ,  Trifluoromethanesulfonic acid Solvents: Dichloromethane ;  2 - 3 h, -40 °C
1.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 17

1152-39-2

87905-98-4

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; overnight, rt
1.2 Reagents: Water ;  0 °C
2.1 Reagents: N-Iodosuccinimide ,  Trifluoromethanesulfonic acid Solvents: Dichloromethane ;  2 - 3 h, -40 °C
2.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 18

220645-86-3

87905-98-4

2227068-13-3

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; overnight, rt
1.2 Reagents: Water ;  0 °C
2.1 Reagents: Tosyl chloride ,  Silver triflate Solvents: Dichloromethane ;  3 h, rt
2.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 19

1125-88-8

28244-98-6

87905-98-4

2227068-13-3

Reaction Conditions

1.1 Catalysts: Camphorsulfonic acid Solvents: Acetonitrile ;  overnight, rt
1.2 Reagents: Trimethylamine ;  rt
2.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; overnight, rt
2.2 Reagents: Water ;  0 °C
3.1 Reagents: Tosyl chloride ,  Silver triflate Solvents: Dichloromethane ;  3 h, rt
3.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

Production Method 20

28244-94-2

87905-98-4

Reaction Conditions

1.1 Reagents: Sodium methoxide Solvents: Methanol ;  overnight, rt
1.2 Reagents: Amberlite IR 120 ;  rt
2.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; overnight, rt
2.2 Reagents: Water ;  0 °C
3.1 Reagents: N-Iodosuccinimide ,  Trifluoromethanesulfonic acid Solvents: Dichloromethane ;  2 - 3 h, -40 °C
3.2 Solvents: Dichloromethane ;  1 h

Reference

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Wu, Chia-Hui; et al, Synlett, 2018, 29(11), 1430-1436

5-Amino-N-benzyloxycarbonylpentanol Raw materials

• 4-Methylphenyl 2,3,4,6-Tetra-O-acetyl-b-D-thioglucopyranoside
• (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate
• 2H-Pyran,tetrahydro-2-(phenylmethoxy)-
• O-[(1,1-Dimethylethyl)diphenylsilyl]-N-[(phenylmethoxy)carbonyl]-L-threonine
• Benzaldehyde dimethyl acetal
• 4-Methylphenylthio-b-D-galactopyranoside
• acetoxime benzoate
• β-D-Galactopyranoside, 4-methylphenyl 2,3-bis-O-(phenylmethyl)-4,6-O-[(S)-phenylmethylene]-1-thio-
• β-D-Galactopyranoside, 4-methylphenyl 4,6-O-[(S)-phenylmethylene]-1-thio-
• 1-Pentanol, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-
• β-D-Glucopyranoside, 4-methylphenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-
• Fmoc-Tyr-OH
• 5-Amino-1-pentanol
• Carbamic acid, N-[(5-hydroxy-2-nitrophenyl)methyl]-N-(5-hydroxypentyl)-, phenylmethyl ester
• 4-Methylphenyl b-D-Thioglucopyranoside

5-Amino-N-benzyloxycarbonylpentanol Preparation Products

• O-[(1,1-Dimethylethyl)diphenylsilyl]-N-[(phenylmethoxy)carbonyl]-L-threonine 5-[[(phenylmethoxy)carbonyl]amino]pentyl ester (2227068-88-2)
• Phenylmethyl N-[5-[[2,3-bis-O-(phenylmethyl)-4,6-O-[(S)-phenylmethylene]-β-D-galactopyranosyl]oxy]pentyl]carbamate (2227068-13-3)
• 5-Amino-N-benzyloxycarbonylpentanol (87905-98-4)

• 1. An approach to asymmetric synthesis of β-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement?
  Piotr Szcze?niak,Sebastian Stecko RSC Adv., 2015,5, 30882-30888
• 2. Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers
  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
• 3. Acenaphthenic hopanoids, a novel series of aromatised
  Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre Albrecht Chem. Commun., 2001, 1976-1977
• 4. An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes?
  Bo Cao,Yin Wei Chem. Commun., 2018,54, 2870-2873
• 5. An aptasensor for the detection of ampicillin in milk using a personal glucose meter
  Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu Zhang Anal. Methods, 2020,12, 3376-3381

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyloxycarbonyls

5-Amino-N-benzyloxycarbonylpentanol (CAS No. 87905-98-4): A Versatile Chemical Building Block for Modern Research

The compound 5-Amino-N-benzyloxycarbonylpentanol (CAS No. 87905-98-4) represents an important N-protected amino alcohol derivative that has gained significant attention in pharmaceutical and biochemical research. This benzyloxycarbonyl (Cbz) protected amino pentanol serves as a crucial intermediate in peptide synthesis and drug discovery, offering researchers a valuable tool for creating complex molecular architectures.

With the growing demand for peptide-based therapeutics and bioconjugation chemistry, 5-Amino-N-Cbz-pentanol has emerged as a key building block in modern medicinal chemistry. Its unique structure combines the reactivity of an amino group protected by the benzyloxycarbonyl group with the versatility of a pentanol chain, making it particularly useful for spacer arm introduction in bioconjugate chemistry and drug delivery system development.

The molecular structure of 5-Amino-N-benzyloxycarbonylpentanol features a five-carbon aliphatic chain terminated by a hydroxyl group at one end and a Cbz-protected amino group at the other. This bifunctional nature allows for selective modifications at either terminus, enabling the creation of various derivatives for different applications. Researchers particularly value this compound for its stability under various reaction conditions while maintaining the potential for selective deprotection when needed.

In the context of current research trends focusing on targeted drug delivery and precision medicine, 5-Amino-N-Cbz-pentanol plays a significant role as a linker molecule. Its ability to serve as a spacer between bioactive molecules and carrier systems has made it valuable in developing antibody-drug conjugates (ADCs) and other advanced therapeutic modalities. The pharmaceutical industry has shown increasing interest in such amino alcohol derivatives as they enable the creation of more stable and effective drug formulations.

The synthesis and application of 5-Amino-N-benzyloxycarbonylpentanol align well with the growing emphasis on green chemistry principles in modern laboratories. Researchers are exploring more efficient synthetic routes to this compound that minimize waste generation and energy consumption. Recent publications have highlighted improved methods for preparing Cbz-protected amino alcohols with higher yields and purity, addressing the needs of both academic and industrial researchers.

Quality control aspects of 5-Amino-N-benzyloxycarbonylpentanol have become increasingly important as its applications expand. Analytical methods such as HPLC, NMR, and mass spectrometry are routinely employed to verify the purity and identity of this compound. The pharmaceutical-grade 5-Amino-N-Cbz-pentanol must meet stringent specifications, especially when used in drug development processes where impurity profiles can significantly impact final product quality.

Storage and handling recommendations for 5-Amino-N-benzyloxycarbonylpentanol typically suggest keeping the material in a cool, dry environment protected from light. While stable under normal conditions, proper storage helps maintain the compound's integrity over extended periods. Researchers appreciate that this N-protected amino pentanol derivative offers good shelf stability compared to some more sensitive amino acid derivatives.

The market for specialized amino alcohol building blocks like 5-Amino-N-benzyloxycarbonylpentanol has shown steady growth, driven by increasing R&D activities in peptide therapeutics and bioconjugation technologies. Custom synthesis services now frequently include this compound in their catalogs, offering various quantities from milligram to kilogram scales to meet diverse research needs. The availability of high-purity Cbz-protected amino alcohols has significantly facilitated progress in multiple areas of chemical biology.

Future research directions involving 5-Amino-N-benzyloxycarbonylpentanol may explore its potential in emerging fields such as proteolysis-targeting chimeras (PROTACs) and other targeted protein degradation technologies. The compound's ability to serve as a flexible linker between different molecular entities positions it as a valuable tool in these cutting-edge therapeutic approaches. Additionally, its applications in material science for creating functionalized surfaces and polymers continue to be investigated.

For researchers working with 5-Amino-N-Cbz-pentanol, understanding its spectral characteristics is crucial for identification and purity assessment. The compound typically shows characteristic peaks in its NMR spectrum, with distinct signals for the benzyloxycarbonyl protecting group and the aliphatic chain protons. These spectroscopic features serve as important quality control markers during synthetic applications and compound characterization.

The development of 5-Amino-N-benzyloxycarbonylpentanol derivatives with modified properties represents an active area of research. Scientists are exploring variations in the carbon chain length, alternative protecting groups, and functional group additions to tailor the compound's properties for specific applications. Such structure-activity relationship studies contribute to the expanding utility of this versatile chemical intermediate in diverse scientific disciplines.

As the scientific community continues to emphasize reproducible research and standardized protocols, detailed documentation of procedures involving 5-Amino-N-benzyloxycarbonylpentanol becomes increasingly valuable. Published methods for its synthesis, purification, and application help establish best practices that enhance research efficiency and reliability across different laboratories working with this important amino alcohol derivative.

• 179320-61-7(Carbamic acid, hexyl-, phenylmethyl ester)
• 69747-36-0(benzyl N-(5-aminopentyl)carbamate)
• 17996-12-2(Cbz-6-aminohexan-1-ol)
• 17996-13-3(4-(Z-Amino)-1-butanol)
• 66095-18-9(N-1-Z-1,6-diaminohexane·HCl)
• 18807-70-0(N,N'-pentane-1,5-diyl-bis-carbamic acid dibenzyl ester)
• 66095-19-0(Carbamic acid, (8-aminooctyl)-, phenylmethyl ester)
• 16644-57-8(Carbamic acid,N,N'-1,6-hexanediylbis-, 1,1'-bis(phenylmethyl) ester)
• 125640-84-8(Carbamic acid, heptyl-, phenylmethyl ester)
• 300660-83-7(Carbamic acid, nonyl-, phenylmethyl ester)