142129-25-7

Basic information

• Product Name: (-)-2--(2S,3R)-3-propyloxirane
• Synonyms: (-)-2--(2S,3R)-3-propyloxirane
• CAS NO: 142129-25-7
• Molecular Weight: 270.35
• Mol File: 142129-25-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (-)-2--(2S,3R)-3-propyloxirane(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2--(2S,3R)-3-propyloxirane(142129-25-7)
• EPA Substance Registry System: (-)-2--(2S,3R)-3-propyloxirane(142129-25-7)

Safety Data

• Hazardous Substances Data: 142129-25-7(Hazardous Substances Data)

Upstream product

• 94992-76-4 (2S,3R)-2,3-epoxy-1-hexanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 928-94-9 (Z)-2-hexen-1-ol 
• 89395-00-6 2,3-epoxyhexan-1-ol 

Downstream Products

• 137369-60-9 (2R*,3S*)-1-(Tosyloxy)-3-chlorohexan-2-ol 
• 137369-61-0 (2R*,3S*)-1-(Tosyloxy)-3-bromohexan-2-ol 
• 188883-02-5 Dibenzyl-((2S,3R)-3-propyl-oxiranylmethyl)-amine 
• 93339-60-7 toluene-4-sulfonic acid (2-hydroxyhexyl) ester 
• 25755-72-0 (+/-)-1-phenylhexan-2-ol 
• 5205-34-5 decan-5-ol 

Relevant articles and documents

Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines

A novel, superbase induced diastereoselective transformation of benzylamino groups containing oxiranes has provided a series of trans-1,2,3-trisubstituted azetidines in good yields. The reaction of the corresponding optically active cis-2,3-disubstituted

Generation of homochiral aziridinium ion intermediates derived from 2,3-epoxy amines: Regiospecific nucleophilic trapping with nitrogen nucleophiles. Application in the synthesis of novel morpholino-sphingolipid analogues with potential glucosylceramide synthase inhibitory activity

The Lewis acid induced rearrangement of 2,3-epoxy amines into the corresponding 2-trimethylsilyloxymethylaziridinium ions is described. Such intermediates have been characterised by 1H NMR spectroscopy, and react with nitrogen nucleophiles regiospecifically to form 1-substituted 2,3-amino alcohols in good to excellent yields and with full stereochemical control. This methodology has been applied to the synthesis of a potential inhibitor of glucosylceramide synthase, a promising target for cancer chemotherapy.

C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Application and Synthesis of Naturally Occuring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide

The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly.In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or threo stereochemistry starting from trans or cis epoxy alcohols.Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occuring (S,S)-2,3-octanediol and (R,R)-muricatacin.The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides.The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols.This methodology has been applied to the asymmetric synthesis of naturally occuring pheromones like 3(R)-octanol and 4(R)-dodecanolide.