Production Method 1

4515-23-5

87219-29-2

Reaction Conditions

1.1 Reagents: Lithium borohydride Catalysts: Sodium borohydride

Reference

Development of chiral β-dicarbonyl equivalents. Enantiodivergent alkylation of aspartic acid

McGarvey, Glenn J.; et al, Tetrahedron Letters, 1983, 24(27), 2733-6

Production Method 2

4515-23-5

87219-29-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  16 h, rt

Reference

A new entry to polyfunctionalized 4,5-trans disubstituted oxazolidin-2-ones from L-aspartic acid

Luppi, Gianluigi; et al, Synlett, 2003, (6), 797-800

Production Method 3

4515-23-5

87219-29-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  0 °C; 16 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

β-Pseudopeptide foldamers. The homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac)

Luppi, Gianluigi; et al, Organic & Biomolecular Chemistry, 2004, 2(15), 2181-2187

Production Method 4

57471-70-2

87219-29-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Ethanol ;  16 h

Reference

Studies towards the total synthesis of batzelladine A

Elliott, Mark C.; et al, Organic & Biomolecular Chemistry, 2004, 2(14), 2003-2011

Production Method 5

130369-36-7

87219-29-2

Reaction Conditions

1.1 Reagents: Glucose ,  Oxygen Catalysts: NADPH ,  Glucose dehydrogenase Solvents: Methanol ,  Water ;  24 h, pH 9, 30 °C

Reference

Baeyer-Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones

Rodriguez-Mata, Maria; et al, Tetrahedron, 2016, 72(46), 7268-7275

Production Method 6

56-84-8

87219-29-2

Reaction Conditions

Reference

L-Aspartic acid

Guevel, Alyx-Caroline, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-2

Production Method 7

1152-61-0

87219-29-2

123673-31-4

Reaction Conditions

1.1 Solvents: Acetic anhydride ;  1 min
1.2 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  16 h, rt

Reference

Introduction of 4(S)-oxazolidineacetic acid, 2-oxo (D-oxac) motif in a polypeptide chain: synthesis and conformational analysis

Luppi, Gianluigi; et al, Organic & Biomolecular Chemistry, 2003, 1(2), 247-250

Production Method 8

133565-44-3

87219-29-2

Reaction Conditions

1.1 Reagents: p-Toluenesulfonic acid Solvents: Benzene

Reference

A facile synthesis of chiral N-protected β-amino alcohols

Rodriguez, Marc; et al, Tetrahedron Letters, 1991, 32(7), 923-6

Production Method 9

56-84-8

87219-29-2

Reaction Conditions

Reference

L-Aspartic Acid

Guevel, Alyx-Caroline, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 10

1152-61-0

87219-29-2

Reaction Conditions

1.1 Reagents: Acetic anhydride ;  1 min
2.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  0 °C; 16 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

β-Pseudopeptide foldamers. The homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac)

Luppi, Gianluigi; et al, Organic & Biomolecular Chemistry, 2004, 2(15), 2181-2187

Production Method 11

1152-61-0

87219-29-2

Reaction Conditions

1.1 Reagents: Acetic anhydride Solvents: Acetic anhydride ;  1 min
2.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  16 h, rt

Reference

A new entry to polyfunctionalized 4,5-trans disubstituted oxazolidin-2-ones from L-aspartic acid

Luppi, Gianluigi; et al, Synlett, 2003, (6), 797-800

Production Method 12

1152-61-0

87219-29-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Ethyl acetate
2.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran
2.2 Reagents: Hydrochloric acid Solvents: Ethanol

Reference

Synthesis of cis-substituted β-lactams, potential intermediates for cis-carbapenems, from L-aspartic acid

Takahashi, Yoshio; et al, Chemical & Pharmaceutical Bulletin, 1986, 34(7), 3020-4

Production Method 13

3479-47-8

87219-29-2

Reaction Conditions

1.1 Reagents: 4-Methylmorpholine ,  Isobutyl chloroformate Solvents: 1,2-Dimethoxyethane
1.2 Reagents: Sodium borohydride Solvents: 1,2-Dimethoxyethane ,  Water
2.1 Reagents: p-Toluenesulfonic acid Solvents: Benzene

Reference

A facile synthesis of chiral N-protected β-amino alcohols

Rodriguez, Marc; et al, Tetrahedron Letters, 1991, 32(7), 923-6

Production Method 14

56-84-8

87219-29-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Ethanol ;  30 min, 0 °C
1.2 16 h, reflux
1.3 Reagents: Sodium carbonate ;  16 h, reflux
1.4 Reagents: Sodium carbonate ;  reflux → 0 °C; 2 h, rt
1.5 Reagents: Hydrochloric acid Solvents: Water ;  neutralized
2.1 Reagents: Sodium borohydride Solvents: Ethanol ;  16 h

Reference

Studies towards the total synthesis of batzelladine A

Elliott, Mark C.; et al, Organic & Biomolecular Chemistry, 2004, 2(14), 2003-2011

Production Method 15

118219-23-1

87219-29-2

35677-89-5

Reaction Conditions

1.1 Reagents: Biphenyl Catalysts: 2,2′-Bipyridine ,  1-Methylimidazole ,  Tempo ,  Copper(1+), tetrakis(acetonitrile)-, (T-4)-, 1,1,1-trifluoromethanesulfonate (1:… Solvents: Acetonitrile ;  6 h, 22 °C
1.2 Solvents: Water ;  15 min, rt

Reference

Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols

Xie, Xiaomin; et al, Journal of the American Chemical Society, 2015, 137(11), 3767-3770

Production Method 16

1152-61-0

87219-29-2

35677-89-5

Reaction Conditions

1.1 Reagents: Calcium chloride ,  Sodium borohydride Solvents: Ethanol ,  Tetrahydrofuran ;  25 °C; 25 °C → 0 °C; 12 h, rt
1.2 Reagents: Citric acid Solvents: Water ;  0 °C
2.1 Reagents: Biphenyl Catalysts: 2,2′-Bipyridine ,  1-Methylimidazole ,  Tempo ,  Copper(1+), tetrakis(acetonitrile)-, (T-4)-, 1,1,1-trifluoromethanesulfonate (1:… Solvents: Acetonitrile ;  6 h, 22 °C
2.2 Solvents: Water ;  15 min, rt

Reference

Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols

Xie, Xiaomin; et al, Journal of the American Chemical Society, 2015, 137(11), 3767-3770

(S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate Raw materials

• N-Cbz-L-aspartic anhydride
• Z-Asp(OBzl)-OH
• benzyl N-(3-oxocyclobutyl)carbamate
• (S)-2-Cbz-aminobutane-1,4-diol
• Z-Asp-OH
• L-Aspartic acid
• diethyl N-benzyloxycarbonyl-(S)-aspartate
• Butanoic acid, 4-hydroxy-3-[[(phenylmethoxy)carbonyl]amino]-, phenylmethyl ester, (3S)-

(S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate Preparation Products

• (S)-Benzyl (2-Oxotetrahydrofuran-3-yl)carbamate (35677-89-5)
• (R)-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid (123673-31-4)
• (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate (87219-29-2)

• 1. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 2. Fast-Track to Research Data Management in Experimental Material Science-Setting the Ground for Research Group Level Materials Digitalization.
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• 4. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 5. Emerging investigators
  Polym. Chem., 2015,6, 5501-5502

• Solvents and Organic Chemicals Organic Compounds Heterocyclic Compounds

Recent Advances in the Study of (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate (CAS: 87219-29-2) in Chemical Biology and Pharmaceutical Research

The compound (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate (CAS: 87219-29-2) has garnered significant attention in recent years due to its potential applications in chemical biology and pharmaceutical research. This chiral building block is particularly notable for its role in the synthesis of biologically active molecules, including protease inhibitors and other therapeutic agents. Recent studies have explored its utility in asymmetric synthesis, drug discovery, and as a precursor for more complex pharmacophores.

One of the key areas of focus has been the development of efficient synthetic routes for (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate. A 2023 study published in the Journal of Medicinal Chemistry demonstrated a novel enzymatic resolution method that significantly improves the enantiomeric purity of the compound, achieving >99% ee. This advancement is critical for its application in the synthesis of high-value pharmaceuticals, where stereochemical integrity is paramount.

In addition to synthetic improvements, recent research has highlighted the compound's role as a versatile intermediate in the construction of gamma-lactam derivatives. These derivatives are of particular interest due to their presence in numerous natural products and FDA-approved drugs. A 2022 paper in Organic Letters detailed a one-pot cascade reaction utilizing (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate to generate diverse gamma-lactam scaffolds with high diastereoselectivity.

The pharmacological potential of derivatives stemming from this compound has also been investigated. Preliminary in vitro studies reported in Bioorganic & Medicinal Chemistry Letters (2023) suggest that certain analogs exhibit promising activity against serine proteases involved in inflammatory pathways. These findings position (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate as a valuable starting point for the development of new anti-inflammatory agents.

From a structural perspective, computational chemistry studies have provided insights into the conformational preferences of this molecule. Density functional theory (DFT) calculations published in The Journal of Physical Chemistry A (2023) reveal that the tetrahydrofuran ring adopts a specific envelope conformation that may influence its reactivity and binding properties in biological systems.

Industrial applications of this compound are also emerging. Several patent applications filed in 2023 describe its use in continuous flow chemistry platforms for the large-scale production of chiral intermediates. These technological developments address previous challenges in scalability while maintaining the compound's stereochemical integrity.

Looking forward, researchers anticipate that (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate will play an increasingly important role in fragment-based drug discovery. Its well-defined stereochemistry, synthetic accessibility, and ability to serve as a scaffold for diverse functionalization make it particularly attractive for this purpose. Ongoing studies are exploring its incorporation into targeted protein degraders (PROTACs) and other emerging therapeutic modalities.

In conclusion, recent advances in the study of (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate (CAS: 87219-29-2) demonstrate its growing importance in both academic and industrial settings. The compound's versatility as a synthetic building block, combined with its potential biological activities, positions it as a valuable tool for medicinal chemistry and drug discovery efforts. Future research directions will likely focus on expanding its applications in asymmetric synthesis and exploring its therapeutic potential through structure-activity relationship studies.

• 1142-20-7(N-[(Benzyloxy)carbonyl]-L-alanine)
• 1155-64-2(H-Lys(Z)-OH)
• 35677-89-5((S)-Benzyl (2-Oxotetrahydrofuran-3-yl)carbamate)
• 29880-21-5(N-Benzyloxycarbonyl-L-aspartic Acid 4-Benzyl Ester)
• 1148-11-4(Carbobenzoxyproline)
• 405-39-0(Z-Lys(Z)-OH)
• 1152-61-0(Z-Asp-OH)
• 1152-62-1(Z-Met-OH)
• 1155-62-0(N-Carbobenzoxy-L-glutamic acid)
• 1149-26-4(N-Cbz-L-valine)