107796-99-6

Basic information

• Product Name: Oxiranecarboxylic acid, 3-propyl-, methyl ester, (2S-trans)- (9CI)
• Synonyms: Oxiranecarboxylic acid, 3-propyl-, methyl ester, (2S-trans)- (9CI)
• CAS NO: 107796-99-6
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.16838
• Product Categories: CARBOXYLICESTER
• Mol File: 107796-99-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Oxiranecarboxylic acid, 3-propyl-, methyl ester, (2S-trans)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranecarboxylic acid, 3-propyl-, methyl ester, (2S-trans)- (9CI)(107796-99-6)
• EPA Substance Registry System: Oxiranecarboxylic acid, 3-propyl-, methyl ester, (2S-trans)- (9CI)(107796-99-6)

Safety Data

• Hazardous Substances Data: 107796-99-6(Hazardous Substances Data)

Upstream product

• 959709-92-3 Methyl (2R,3R)-2-chloro-3-hydroxyhexanoate 
• 106498-75-3 2,3-epoxyhexanol 
• 186581-53-3 diazomethane 
• 92418-71-8 (2R,3R)-2,3-epoxy-1-hexanol 
• 89321-71-1 (2S,3S)-3-propyl-2-oxiranemethanol 
• 96096-69-4 3-propylepoxyethane-2-carboxylic acid 

Downstream Products

• 139618-99-8 (2R,3S)-1-(3,5-Dinitro-benzoyl)-3-propyl-aziridine-2-carboxylic acid methyl ester 
• 31323-51-0 (S)-γ-Propyl-γ-butyrolactone 

Relevant articles and documents

PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-2 -HYDROXYPROPIONIC CYCLOPROPYLAMIDE DERIVATIVES AND SALTS THEREOF

An objective of the present application is to provide an industrially practicable method for producing an optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof from an inexpensive easily-available starting material. The derivative or salt thereof is useful as an intermediate for a medicine. It is also intended by the present application to provide a useful intermediate of the derivative. The objective is attained by the following method. First, an easily-available 2-halo-3-oxopropionic acid derivative is asymmetrically reduced, and then epoxidated to produce an optically-active epoxycarboxylic acid derivative. Next, the derivative is converted into an optically-active epoxyamide derivative by reaction with cyclopropylamine, and then reacted with a nitrile to obtain an optically-active oxazolinamide derivative. Subsequently, selective acid solvolysis of the oxazoline skeleton gives the optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof.

A convenient synthesis of aziridine-2-carboxylic esters

Optically active oxirane-2-carboxylic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide.The azido alcohols obtained were subsequently converted into aziridine-2-carboxylic esters by reaction with triphenylphosphine, in good yields and with high optical purity.Various racemic oxirane-2-carboxylic esters were subjected to the same sequence of reactions.

A CONVENIENT SYNTHESIS OF OPTICALLY ACTIVE 1H-AZIRIDINE-2-CARBOXYLIC ACIDS (ESTERS).

Optically active glycidic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide.In a subsequent reaction with PPh3 the azido alcohols thus obtained were converted into aziridine-2-carboxylic esters of high optical purity in good yields.

Synthesis of the optical antipodes of 4-alkyl-γ-lactones

Optical antipodes of 4-alkyl-γ-lactones 3 have been prepared by photochemical rearrangement of optically active α,β-epoxy diazomethyl ketones 1 in ethanol to give 4-hydroxy-alkenoates 2, followed by reduction of the alkene bond and subsequent lactonization.The required epoxy diazomethyl ketones 1 were obtained via the following sequence of reactions: alkylation of 2-propyn-1-ol, subsequent reduction to the alkenols 6, Sharpless epoxidation to 2,3-epoxy alcohols 7, oxidation to glycidic esters 8 and finally conversion to diazo ketones 1.The enantiomeric purities range from 84 to 100percent.

Enantioselective Diastereospecific Synthesis of anti-α-Alkyl-β-hydroxy Esters through Cuprate Opening of Glycidic Esters

A diastereospecific chain elongation of the aldehydes 1 to anti-αalkyl-β-hydroxy esters 2 via the intermediates 4 - 7 is described.By means of the Sharpless epoxidation, 2 may be obtained with >90percent ee in either enantiomer.