249765-15-9

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 74-88-4 methyl iodide 
• 4248-19-5 tert-butyl carbazate 
• 249765-14-8 Methyl 2-azido-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-isopropylidene-L-lyxonate 
• 205449-11-2 (S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester 
• 205449-09-8 Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester 
• 205449-10-1 Methyl 5-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-L-xylonate 
• 657404-83-6 tert-butyl N-(1S)-1-[(4S,5S)-5-([1-(tert-butyl)-1,1-diphenylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-nitroethylcarbamate 
• 101331-92-4 4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose 
• 657404-82-5 tert-butyl N-[(R)-1-[(4R,5S)-5-([1-(tert-butyl)-1,1-diphenylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(phenylsulfonyl)methyl]carbamate 

Relevant academic research and scientific papers

Highly diastereoselective addition of nitromethane anion to chiral α-amidoalkylphenyl sulfones. Synthesis of optically active α-amino acid derivatives

Optically active syn-α-amidoalkylphenyl sulfones can be prepared from chiral aldehydes in anhydrous conditions using benzenesulfinic acid. These sulfones in basic conditions give N-acylimines that react with sodium methane-nitronate to afford the corresponding nitro adducts with high anti diastereoselectivity. PM3 semiempirical calculations provide a rationale for the observed opposite stereoselectivitity. The obtained nitro derivatives undergo a Nef reaction followed by a methylation giving optically active β-hydroxy-α-amino acid and α,β-diamino acid esters in good yield. These amino acid derivatives are important building blocks for the preparation of biologically active compounds.

A convenient synthesis of a N-protected l-carbamoylpolyoxamic acid derivative: Total synthesis of (+)-polyoxin J and (+)-polyoxin L1

A convenient synthesis of the N-protected L-carbamoylpolyoxamic acid derivative 7 from 4-O-tert-butyldiphenylsilyl-2,3-isopropylidene-L-threose (8) using vinylmagnesium bromide and its application to the total syntheses of the peptidyl nucleoside antibiotics, polyoxins J (1) and L (2), are described.