172277-26-8

Basic information

• Product Name: Oxiranecarboxylic acid, 3-propyl-, ethyl ester, (2S-trans)- (9CI)
• Synonyms: Oxiranecarboxylic acid, 3-propyl-, ethyl ester, (2S-trans)- (9CI)
• CAS NO: 172277-26-8
• Molecular Formula: C8H14O3
• Molecular Weight: 158.19496
• Product Categories: CARBOXYLICESTER
• Mol File: 172277-26-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Oxiranecarboxylic acid, 3-propyl-, ethyl ester, (2S-trans)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranecarboxylic acid, 3-propyl-, ethyl ester, (2S-trans)- (9CI)(172277-26-8)
• EPA Substance Registry System: Oxiranecarboxylic acid, 3-propyl-, ethyl ester, (2S-trans)- (9CI)(172277-26-8)

Safety Data

• Hazardous Substances Data: 172277-26-8(Hazardous Substances Data)

Upstream product

• 172170-24-0 ethyl (2R,3R)-2-chloro-3-hydroxyhexanoate 
• 28942-46-3 Ethyl 3-chloro-2-oxohexanoate 

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.

Stereospecific preparation of glycidic esters from 2-chloro-3-hydroxyesters. Application to the synthesis of (2R,3R)-3-phenylisoserine

Cis- and trans-glycidic esters may be synthesized in high enantiomeric purities by cyclisation with potassium carbonate in DMF of the corresponding syn- or anti-2-chloro-3-hydroxyesters, prepared by microbial reduction of 2-chloro-3-oxoesters. In contrast, more basic media such as sodium ethylate afford exclusively the trans-isomer, whatever the stereochemistry of the starting 2-chloro-3-hydroxyester is. Cyclisation of deuterated compounds showed that this result was due to a rapid isomerisation of the syn esters into anti isomers before cyclisation. An application of this reaction to the synthesis of (2R,3R)-3-phenylisoserine is described.

Highly Enantioselective Reduction of 3-Chloro-2-oxoalkanoates with Fermenting Bakers' Yeast. A New Synthesis of Optically Active 3-Chloro-2-hydroxyalkanoates and Glycidic Esters

Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn(2S,3S) = 52:48-90:10) in 50-85percent yields with > 95percent ee except for 43percent ee of ethyl syn-(2S,3S)-3-chloro-2-hydroxy-4-phenylbutanoate (2j).Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66percent yields with 44-64percent ee.Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86percent ee in high yields.