121357-96-8

Basic information

• Product Name: methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate
• Synonyms: methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate
• CAS NO: 121357-96-8
• Molecular Weight: 280.321
• Mol File: 121357-96-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate(121357-96-8)
• EPA Substance Registry System: methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate(121357-96-8)

Safety Data

• Hazardous Substances Data: 121357-96-8(Hazardous Substances Data)

Upstream product

• 84379-51-1 2-O-benzyl-L-threitol 
• 100-52-7 benzaldehyde 
• 38270-72-3 dimethyl 2,3-O-benzylidene-L-tartrate 
• 67-56-1 methanol 
• 100906-42-1 2-O-benzyl-3,4-O-isopropylidene-L-threose 
• 92973-39-2 O³,O⁴-(1-methylethylidene)-L-threonic acid 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 84379-53-3 2-O-benzyl-3,4-O-isopropylidene-L-threitol 
• 100-39-0 benzyl bromide 
• 92973-40-5 methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate 
• 104333-70-2 (2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 100906-42-1 2-O-benzyl-3,4-O-isopropylidene-L-threose 
• 1443340-48-4 (2R,3S)-2-benzyloxy-3-hydroxybutyrolactone 
• 464203-98-3 dimethyl (1R,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate 
• 464203-96-1 dimethyl (1S,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate 

Relevant articles and documents

Stereoselective total synthesis of both (6R,9R,10S,7E)- and (6S,9R,10S,7E)-epimers of oxylipin (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid

An asymmetric synthesis of both the stereoisomers (2a & 2b) of the structure 2 proposed for (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid, an immunostimulant oxylipin from the n-butanol extract of the corms of Dracontium loretense, has been accomplished. The key steps involved are using Jacobsen's hydrolytic kinetic resolution (HKR), Julia-Kocienski olefination, regioselective epoxide ring opening and Wittig olefination. The configuration (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid was established as 2a from comparison of NMR data, HPLC analysis and [α]D values of naturally derived (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid, and comparison with the synthetic diastereomers 2a and 2b.

Synthesis of (1R,2S)- and (1S,2S)-3-azido-1,2-dihydroxypropylphosphonates

An efficient synthesis of diastereomerically pure dimethyl (1R,2S)- and (1S,2S)-3-azido-1,2-dihydroxypropylphosphonates from L-ascorbic acid, via new chirons: (2S,3S)-4-azido-3-benzyloxy-1,2-O-isopropylidene-1,2-butanediol and (2S)-3-azido-2-benzyloxypropanal was elaborated.

Convenient One-Pot Conversion of Alcohols into Esters via Hemiacetal Intermediates

A simple and efficient one-pot oxidative procedure, adaptable to a large scale, is described for the preparation of methyl esters from either primary alcohols or vic-diols.The aldehyde is generated by Swern or periodate oxidation, followed by bromine oxidation of the methyl hemiacetal formed in aqueous methanolic solution.