126360-34-7

Basic information

• Product Name: (3S,4S)-4-O-benzyloxymethyl-3-O-tert-butyldimethylsilyl-1-(2-thiazolyl)-pent-1-ene
• CAS NO: 126360-34-7
• Molecular Weight: 419.66
• Mol File: 126360-34-7.mol

Chemical Properties

• CAS DataBase Reference: (3S,4S)-4-O-benzyloxymethyl-3-O-tert-butyldimethylsilyl-1-(2-thiazolyl)-pent-1-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-4-O-benzyloxymethyl-3-O-tert-butyldimethylsilyl-1-(2-thiazolyl)-pent-1-ene(126360-34-7)
• EPA Substance Registry System: (3S,4S)-4-O-benzyloxymethyl-3-O-tert-butyldimethylsilyl-1-(2-thiazolyl)-pent-1-ene(126360-34-7)

Safety Data

• Hazardous Substances Data: 126360-34-7(Hazardous Substances Data)

Upstream product

• 115754-94-4 thiazol-2-ylmethyltriphenylphosphonium chloride 
• 126360-32-5 2-O-tert-butyldimethylsilyl-3-O-benzyloxymethyl-4-deoxy-L-threose 
• 104470-50-0 (S)-2-Benzyloxymethoxy-1-thiazol-2-yl-propan-1-ol 
• 126360-31-4 (1R)-1-O-tert-butyldimethylsilyl-2-O-benzyloxymethyl-3-deoxy-1-(2-thiazolyl)-L-glycitol 
• 126360-30-3 2-<(S)-2-(benzyloxymethoxy)propanoyl>thiazole 
• 63296-55-9 (S)-(-) ethyl 2-<(benzyloxy)ymethoxy>propanoate 

Downstream Products

• 126360-35-8 2,3,6-trideoxy-4-O-tert-butyldimethylsilyl-5-O-benzyloxymethyl-L-threo-hexose 

Relevant articles and documents

A CONCISE THIAZOLE MEDIATED SYNTHESIS OF L-(-)-RHODINOSE FROM (S)-ETHYL LACTATE. THE THIAZOLE ROUTE TO DEOXYSUGARS

2-Lithiothiazole (2-LTT) (1a) and 2-thiazolylmethylenetriphenylphosphorane (2-TMP) (1b) are employed as aldehyde equivalents in a new concise synthesis of 4-O-tert-butyldimethylsilyl L-(-)-rhodinose (2b) from (S)-ethyl lactate.The key intermediates in the synthesis are two differentially protected hydroxyl aldehydes, i.e. the 4-deoxy-L-threose derivative 3b and the (S,S)-4,5-dihydroxyhexanal derivative 4b which are obtained in high yield starting from O-benzyloxymethyl (S)-ethyl lactate (5).The selective C5 hydroxyl deprotection in 4b leads to the TBS-protected rhodinose 2b in the pyranose form.A complete (1)H and (13)C NMR analysis of 2b is provided.

ORGANIC SYNTHESIS WITH SULFUR HETEROCYCLES (THIAZOLES) AS AUXILIARIES. THE THIAZOLE ROUTE TO CARBOHYDRATES AND BIOLOGICALLY ACTIVE DERIVATIVES

Funcionally-substituted thiazoles at C-2, namely 2-trimethylsilylthiazole, (2-TST), 2-thiazolylmethylenetriphenylphosphorane (2-TMP), and 2-thiazolylcarbonitrile N-oxide (2-TNO) serve as effective auxiliaries in new synthetic strategies for the stereoselctive synthesis (THIAZOLE ROUTE) of long-chain protected polyhydroxyaldehydes, i.e. carbohydrate-like materials, starting from readily available precursors such as chiral hydroxy- and aminoaldehydes.These methodologies are based on two essential operations, both chemically and stereochemically very efficient; i) the coupling between the functionally-substituted thiazole and an appropiate substrate by a carbon-carbon bond forming reaction; ii) the aldehyde release in the resulting adduct by thiazole into formyl conversion.Some compounds obtained in this way are transformed by functional group elaborations into molecules of biological relevance such as deoxy- and aminosugars, and sphingosines.