192129-70-7

Upstream product

• 192129-55-8 (4R,5R)-5-((R)-3-Benzyloxycarbonylamino-1-methyl-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 192129-51-4 (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((R)-1-methyl-3-oxo-propyl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 192129-52-5 (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((R)-3-hydroxy-1-methyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 182962-13-6 (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-3-oxo-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 176967-05-8 (4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 138319-97-8 3-<(tert-Butoxycarbonyl)amino>-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-N,2-O-isopropylidene-D-threose 

Relevant academic research and scientific papers

Formal synthesis of an unusual amino acid component of cyclosporin, involving stereocontrolled nucleophilic 1,4-addition

A syn-(2R)-amino-1,3,4-butanetriol derivative, readily available from D-isoascorbic acid, was utilized for the synthesis of MeBmt found in the immunosuppressive undecacyclopeptide cyclosporin. This new strategy involves diastereoselective nucleophilic 1,4-addition of lithium dimethylcuprate to a chiral α,β-unsaturated aldehyde, and elaboration of the terminal double bond, by Takai or Wittig method for the MeBmt or its 6Z-isomer, respectively.