Production Method 1

33106-64-8

81445-44-5

Reaction Conditions

1.1 Reagents: 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide Solvents: Ethyl acetate ;  3.25 h, 80 °C

Reference

Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines

Gutierrez, David A.; et al, Organic Letters, 2022, 24(5), 1164-1168

Production Method 2

33106-64-8

81445-44-5

Reaction Conditions

1.1 Reagents: 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide Solvents: Ethyl acetate ;  rt → reflux; 4 h, reflux

Reference

Acyclic Stereocontrol in the Additions of Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines

Moore, Lucas C. ; et al, Chemistry - A European Journal, 2019, 25(52), 12214-12220

Production Method 3

54783-72-1

81445-44-5

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ;  30 min, -78 °C
1.2 Reagents: Potassium sodium tartrate Solvents: Water ;  -78 °C → rt

Reference

Botcinolide/botcinin: asymmetric synthesis of the key fragments

Ramirez-Fernandez, Jacinto; et al, Natural Product Communications, 2011, 6(4), 443-450

Production Method 4

122151-33-1

81445-44-5

Reaction Conditions

1.1 Reagents: Vitride Solvents: Tetrahydrofuran

Reference

An improved synthetic method of (S)-2-alkoxypropanals from ethyl (S)-lactate

Kobayashi, Yuko; et al, Bulletin of the Chemical Society of Japan, 1989, 62(9), 3038-40

Production Method 5

81927-55-1

687-47-8

81445-44-5

Reaction Conditions

1.1 Reagents: Trifluoromethanesulfonic acid Solvents: Dichloromethane ,  Cyclohexane
1.2 Reagents: Diisobutylaluminum hydride Solvents: Toluene ,  Tetrahydrofuran ;  -78 °C

Reference

Exploring the Solid-Phase Synthesis of 3,4-Disubstituted β-Lactams: Scope and Limitations

Delpiccolo, Carina M. L.; et al, Journal of Combinatorial Chemistry, 2005, 7(2), 331-344

Production Method 6

81927-55-1

687-47-8

81445-44-5

Reaction Conditions

1.1 Reagents: Trifluoromethanesulfonic acid Solvents: Dichloromethane ,  Cyclohexane ;  rt; 60 h, rt
2.1 Reagents: Diisobutylaluminum hydride Solvents: Diethyl ether ,  Hexane ;  -78 °C; 2 h, -78 °C

Reference

Volatile Lactones from Streptomycetes Arise via the Antimycin Biosynthetic Pathway

Riclea, Ramona; et al, ChemBioChem, 2012, 13(11), 1635-1644

Production Method 7

77287-11-7

81445-44-5

Reaction Conditions

1.1 Solvents: Dichloromethane ;  rt → -78 °C
1.2 Reagents: Diisobutylaluminum hydride Solvents: Toluene ;  -78 °C; 1 h, -78 °C; -78 °C

Reference

Stereoselective synthesis of functionalized triol units by SnCl4 promoted allylation of α-benzyloxyaldehydes: crucial role of the stoichiometry of the Lewis acid

Dubost, Christophe; et al, Tetrahedron, 2004, 60(35), 7693-7704

Production Method 8

77287-11-7

81445-44-5

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ,  Hexane ;  -78 °C; 6 h, -78 °C
1.2 Reagents: Potassium sodium tartrate Solvents: Water ;  -78 °C; -78 °C → rt; 1 h, rt

Reference

Studies Towards the Total Synthesis of Lactonamycin: Investigations into Glycosidation Reactions

Rzepa, Paula Rocha, 2008, , ,

Production Method 9

81445-44-5

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol

Reference

Palladium on Carbon

King, Anthony O.; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 10

687-47-8

81445-44-5

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  20 min, 0 °C
1.2 0 °C → rt; 12 h, rt
1.3 Reagents: Water ;  rt
2.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ,  Toluene ;  25 min, -78 °C; 1 h, -78 °C
2.2 Reagents: Potassium sodium tartrate Solvents: Water ;  1 h, rt

Reference

Direct Deprotonative Functionalization of α,α-Difluoromethyl Ketones using a Catalytic Organosuperbase

Messara, Amelia; et al, Angewandte Chemie, 2023, 62(10),

Production Method 11

3913-64-2

81445-44-5

Reaction Conditions

Reference

The first total synthesis of phomopsolidone A

Raju, Kasa Shiva; et al, Tetrahedron Letters, 2016, 57(19), 2109-2111

Production Method 12

122151-32-0

81445-44-5

Reaction Conditions

1.1 Reagents: Vitride Solvents: Toluene ;  5 h, < rt
1.2 Reagents: Acetone

Reference

Stereoselective Grignard additions to N-formyl hydrazone: a concise synthesis of NoxafilR side chain and a synthesis of NoxafilR

Saksena, Anil K.; et al, Tetrahedron Letters, 2004, 45(44), 8249-8251

Production Method 13

122151-32-0

81445-44-5

Reaction Conditions

1.1 Reagents: Vitride Solvents: Toluene ;  30 min, -12 °C; 2.5 h, -13 - -10 °C
1.2 Solvents: Acetone ;  10 min, -13 - -10 °C

Reference

Efficient Stereoselective Synthesis of a Key Chiral Aldehyde Intermediate in the Synthesis of Picolinamide Fungicides

Li, Fangzheng ; et al, Organic Process Research & Development, 2019, 23(10), 2253-2260

Production Method 14

122151-33-1

81445-44-5

Reaction Conditions

1.1 Reagents: Vitride Solvents: Toluene ,  Tetrahydrofuran

Reference

(S)-Ethyl lactate

Grabowski, Edward J. J., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-4

Production Method 15

81927-55-1

687-47-8

81445-44-5

Reaction Conditions

1.1 Catalysts: Trifluoromethanesulfonic acid
1.2 Reagents: Diisobutylaluminum hydride

Reference

Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction

Gazaille, Jeffrey A.; et al, Organic Letters, 2012, 14(1), 178-181

Production Method 16

81445-44-5

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol

Reference

Palladium on carbon

King, Anthony O.; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-5

Production Method 17

81445-44-5

Reaction Conditions

1.1 Catalysts: Palladium Solvents: Methanol
1.2 Reagents: Hydrogen

Reference

Synthesis of the four stereoisomers of 1,1,1-trifluorobutane-2,3-diol

Morelli, Carlo F.; et al, Organic Preparations and Procedures International, 2002, 34(1), 103-107

Production Method 18

53346-03-5

81445-44-5

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Toluene ;  -50 °C; 2.5 h, -50 °C
1.2 Reagents: Sodium pyrosulfite Solvents: Water ;  -50 °C; -50 °C → 20 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 11, 0 °C

Reference

Intermolecular 1,3-dipolar cycloadditions of azomethine imines

Jones, Raymond C. F.; et al, ARKIVOC (Gainesville, 2007, (5), 152-166

Production Method 19

105299-38-5

81445-44-5

Reaction Conditions

1.1 Reagents: Boron trifluoride ,  Mercuric oxide Solvents: Diethyl ether

Reference

Bakers' yeast-mediated synthesis of protected α-hydroxy aldehydes

Guanti, Giuseppe; et al, Journal of the Chemical Society, 1986, (2), 138-40

Production Method 20

687-47-8

81445-44-5

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide
1.2 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ;  -90 °C

Reference

Effect of substituents on the ring-closing metathesis reaction in the synthesis of functionalized nonanolactones

Ramirez-Fernandez, Jacinto; et al, Synlett, 2008, (3), 339-342

Production Method 21

687-47-8

81445-44-5

Reaction Conditions

1.1 Reagents: Silver oxide (Ag2O) Solvents: Diethyl ether ;  10 h, 40 °C
2.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ;  30 min, -78 °C
2.2 Reagents: Methanol

Reference

Luquilloamides, Cytotoxic Lipopeptides from a Puerto Rican Collection of the Filamentous Marine Cyanobacterium Oscillatoria sp.

Kim, Geum Jin; et al, Journal of Organic Chemistry, 2022, 87(2), 1043-1055

Production Method 22

87604-55-5

81445-44-5

Reaction Conditions

1.1 Catalysts: Lead tetraacetate

Reference

On the steric course of the addition of some organometallic reagents to (R)-2,3-O-isopropylideneglyceraldehyde. Synthesis of optically active α-benzyloxy aldehydes, alcohols, carboxylic acids and 1,2-diols

Mulzer, Johann; et al, Tetrahedron Letters, 1983, 24(28), 2843-6

Production Method 23

1234714-02-3

81445-44-5

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  -15 °C; 1 h, -15 °C
1.2 Reagents: Water ;  pH 7, 0 °C
1.3 Reagents: (-)-Camphorsulfonic acid Solvents: Pentane ;  1 h, rt

Reference

Alkylation and aldol reactions of acyl derivatives of N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: asymmetric synthesis of α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes

Chernega, Alexander N.; et al, Tetrahedron, 2010, 66(23), 4167-4194

Production Method 24

33106-64-8

81445-44-5

Reaction Conditions

1.1 Reagents: 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide Solvents: Ethyl acetate ;  rt → 80 °C; 3.25 h, 80 °C

Reference

Diastereoselective addition of prochiral nucleophilic alkenes to α-chiral N-sulfonyl imines

Gutierrez, David A.; et al, ChemRxiv, 2021, 1, 1-6

Production Method 25

54783-72-1

81445-44-5

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Diethyl ether ,  Hexane ;  -78 °C; 1.5 h, -78 °C
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

A highly stereoselective ether directed palladium catalyzed aza-Claisen rearrangement

Jamieson, Andrew G.; et al, Organic & Biomolecular Chemistry, 2005, 3(5), 735-736

Production Method 26

54783-72-1

81445-44-5

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Diethyl ether ,  Hexane ;  1.5 h, -78 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C

Reference

Synthesis of (-)-(E,S)-3-(benzyloxy)-1-butenyl phenyl sulfone via a Horner-Wadsworth-Emmons reaction of (-)-(S)-2-(benzyloxy)propanal

Enders, D.; et al, Organic Syntheses, 2002, 78, 177-188

(2S)-2-(benzyloxy)propanal Raw materials

• (S)-2-(Benzyloxy)-1-(pyrrolidin-1-yl)propan-1-one
• Propanal, 2-hydroxy-, (S)-
• Benzyl 2,2,2-trichloroacetimidate
• 1,2-Butanediol, 3-(phenylmethoxy)-, (2R,3S)-
• Methyl 2-(Benzyloxy)propanoate
• Propanoic acid, 2-(phenylmethoxy)-, methyl ester, (2S)-
• (-)-Ethyl L-Lactate
• Propanamide, N,N-dimethyl-2-(phenylmethoxy)-, (2S)-
• Propanamide, N-(1,1-dimethylethoxy)-N-[(1R)-1-(1-naphthalenyl)ethyl]-2-(phenylmethoxy)-, (2S)-
• Ethyl (S)-2-(Benzyloxy)propionate
• 2-Propanol, 1,1-bis[(4-methylphenyl)thio]-
• (S)-2-(Benzyloxy)propan-1-ol

(2S)-2-(benzyloxy)propanal Preparation Products

• (2S)-2-(benzyloxy)propanal (81445-44-5)

• 1. Excited-state proton-coupled electron transfer within ion pairs?
  Gerald J. Meyer,Leif Hammarstr?m Chem. Sci., 2020,11, 3460-3473
• 2. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147
• 3. 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
• 4. 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
• 5. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788

Chemical Profile of (2S)-2-(benzyloxy)propanal (CAS No. 81445-44-5)

(2S)-2-(benzyloxy)propanal, identified by the Chemical Abstracts Service Number (CAS No.) 81445-44-5, is a significant compound in the realm of organic chemistry and pharmaceutical research. This chiral aldehyde derivative has garnered attention due to its structural versatility and potential applications in synthetic chemistry and drug development. The compound’s stereochemistry, specifically its (S)-configuration at the prochiral carbon, makes it a valuable intermediate in the synthesis of enantiomerically pure molecules, which are increasingly critical in modern medicinal chemistry.

The molecular structure of (2S)-2-(benzyloxy)propanal consists of a propanal backbone substituted with a benzyloxy group at the second carbon position. This configuration imparts unique reactivity, making it a useful building block for constructing more complex molecules. The benzyloxy group enhances solubility in polar organic solvents while maintaining the reactivity of the aldehyde functionality, which is pivotal for further functionalization via oxidation, reduction, or condensation reactions.

In recent years, (2S)-2-(benzyloxy)propanal has been explored in the context of developing novel pharmacophores. Its chiral center allows for the synthesis of enantiomerically enriched derivatives, which are often preferred in drug design due to improved selectivity and reduced side effects. For instance, researchers have utilized this compound as a precursor in the synthesis of protease inhibitors, where precise stereochemical control is essential for efficacy. The benzyloxy moiety also facilitates interactions with biological targets, making it a promising candidate for designing molecules with enhanced binding affinity.

One of the most compelling aspects of (2S)-2-(benzyloxy)propanal is its role in asymmetric synthesis. The (S)-configuration at the chiral center ensures that downstream reactions yield products with high enantiomeric purity, which is crucial for pharmaceutical applications. Recent advances in catalytic asymmetric methods have further highlighted the utility of this compound. For example, transition-metal-catalyzed cross-coupling reactions employing (2S)-2-(benzyloxy)propanal have enabled the construction of complex heterocyclic frameworks with high yields and excellent diastereoselectivity.

The pharmaceutical industry has shown particular interest in derivatives of (2S)-2-(benzyloxy)propanal due to their potential as drug candidates. Studies have demonstrated its utility in generating novel analogs with anti-inflammatory, anti-microbial, and anti-cancer properties. The aldehyde group can be further modified to introduce additional functionalities such as carboxylic acids, esters, or amides, broadening its applicability. Additionally, the benzyloxy group can serve as a handle for further derivatization via palladium-catalyzed coupling reactions, allowing for the introduction of aryl or heteroaryl groups into the molecular framework.

From a synthetic chemistry perspective, (2S)-2-(benzyloxy)propanal represents an efficient entry point to a diverse array of structures. Its straightforward preparation from readily available starting materials makes it an attractive choice for both academic and industrial research laboratories. The compound’s stability under various reaction conditions further enhances its practicality as an intermediate. Moreover, recent reports highlight its use in flow chemistry setups, where controlled reaction conditions improve reproducibility and scalability.

The role of chirality in biological activity cannot be overstated, and (2S)-2-(benzyloxy)propanal exemplifies this principle. Enantiomerically pure compounds often exhibit distinct pharmacological profiles compared to their racemic counterparts. This has spurred interest in developing efficient methods for producing enantiomerically enriched derivatives on a large scale. Advances in biocatalysis have also opened new avenues for synthesizing chiral compounds like (2S)-2-(benzyloxy)propanal, leveraging enzymes such as ketoreductases or transaminases to achieve high enantiomeric excess with minimal byproducts.

In conclusion,(2S)-2-(benzyloxy)propanal (CAS No. 81445-44-5) is a versatile and valuable compound with significant implications in pharmaceutical research and synthetic chemistry. Its unique structural features—combining a chiral center with an aldehyde and benzyloxy functionality—make it an ideal candidate for generating enantiomerically pure molecules with potential therapeutic applications. As research continues to uncover new synthetic strategies and biological targets,(2S)-2-(benzyloxy)propanal is poised to remain at the forefront of chemical innovation.

• 87678-65-7(Hexanal, 2-(phenylmethoxy)-, (S)-)
• 100836-85-9((2R)-2-(benzyloxy)propanoic acid)
• 113133-46-3(3-(BENZYLOXY)BUTAN-2-ONE)
• 53346-05-7(Propanal, 2-(phenylmethoxy)-)
• 89279-49-2(Butanal, 2-(phenylmethoxy)-)
• 81445-45-6(Propanal, 2-(phenylmethoxy)-, (2R)-)
• 129492-58-6((S)-2-(Benzyloxy)-3-hydroxypropanal)
• 97203-22-0(2-Butanone, 3-(phenylmethoxy)-, (3S)-)
• 63296-56-0(Propanal, 2-[(phenylmethoxy)methoxy]-, (2S)-)
• 60656-87-3(2-(Benzyloxy)acetaldehyde)