132682-38-3

Upstream product

• 132682-37-2 (R)-2-Oxo-4-((Z)-styryl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 132639-29-3 tert-butyl 2,2-dimethyl-4-[(Z)-2-phenylethenyl]-1,3-oxazolane-3-carboxylate 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 132682-35-0 (Z)-(R)-(+)-3-(2'-phenyl-1'-ethylenyl)-2-oxazolidinone 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 709026-61-9 (E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine 

Downstream Products

• 132682-39-4 (Z)-(R)-2-tert-Butoxycarbonylamino-4-phenyl-but-3-enoic acid 
• 214556-67-9 ((1S,2S,3R)-2,3-Dihydroxy-1-hydroxymethyl-3-phenyl-propyl)-carbamic acid tert-butyl ester 
• 214556-66-8 ((1S,2R,3S)-2,3-Dihydroxy-1-hydroxymethyl-3-phenyl-propyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

A short and efficient synthesis of phytosphingosines using asymmetric dihydroxylation

A short synthesis of the phytosphingosine derivatives and their stereoisomers by using asymmetric dihydroxylation of the optically active olefins derived from L-serine is described.

Synthesis of Chiral Vinylglycines

(R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8.Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (>95percent ee) and double-bond geometry.D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives β,γ-unsaturated amino acids with the L configuration.The double-bond geometry is controlled by the nature of the phosphorous ylide employed.The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.

A NEW NUCLEOPHILIC ALANINOL SYNTHON FROM SERINE

A new nucleophilic alaninol synthon derived from serine is reported.The utility of this reagent in the stereoselective synthesis of β,γ-unsaturated amino alcohols is described.