115889-53-7

Basic information

• Product Name: (1R)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol
• CAS NO: 115889-53-7
• Molecular Weight: 434.557
• Mol File: 115889-53-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1R)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol(115889-53-7)
• EPA Substance Registry System: (1R)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol(115889-53-7)

Safety Data

• Hazardous Substances Data: 115889-53-7(Hazardous Substances Data)

Upstream product

• 115822-48-5 (S,S)-2-<(tert-butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1(1,3-thiazol-2-yl)propan-1-ol 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 115843-62-4 (S)-4-((S)-Benzyloxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 115822-52-1 (1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol 
• 115822-55-4 (4S,1'S)-4-(1'-benzyloxy-2'-oxoethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 79265-30-8 2-(trimethylsilyl)thiazole 

Downstream Products

• 124127-34-0 2-O-Acetyl-4-amino-3-O-benzyl-4-N-(tert-butoxycarbonyl)-4-deoxy-4,5-N,O-isopropylidene-L-arabinose 
• 124127-32-8 (S)-4-((1S,2R)-2-Acetoxy-1-benzyloxy-2-thiazol-2-yl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

Stereochemistry Associated with the Addition of 2-(Trimethylsilyl)thiazole to Differentially Protected α-Amino Aldehydes. Applications toward the Synthesis of Amino Sugars ans Sphingosines

The stereochemistry and synthetic utility of the addition of 2-(trimethylsilyl)thiazole (2-TST, 1) to various N-protected α-amino aldehydes is described.The reactions of 1 with N-Boc-L-serinal acetonide (2) and N-Boc-L-threoninal acetonide (3) are essential anti diastereoselective (ds = 85-90percent) in agreement with the Felkin-Anh model for asymmetric induction, whereas the reactions with O-benzyl-NH-Boc-L-serinal (4) and NH-Boc-L-phenylalaninal (5) are syn diastereoselective (ds = 80percent).The reversal of diastereoselectivity is interpreted on the basis of a proton-bridged cyclic Cram model for asymmetric induction.Te anti-adduct derived the N-Boc-L-serinal acetonide (2) was subjected to thiazol-to-formyl unmasking to give a one-carbon higher homologue (i. e., the O,N-protected β-amino-α-hydroxy aldehyde 6a).This material serves as a precursor to ribo- and arabino-4-amino-4-deoxypentoses via a further one-carbon-chain elongation with 2-TST and to a C20 sphingosine via Wittig olefination.The above ribo-amino sugar was transformed via sequential Wittig olefination and reduction into a C18 phytosphingosine.