205449-13-4

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 110426-21-6 (E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one 
• 110426-22-7 5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol 
• 605668-77-7 5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol 
• 605668-78-8 4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane 
• 605668-79-9 4-[1-azido-2-benzyloxy-(1R)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane 
• 610316-26-2 [(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol 
• 610316-28-4 {1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl}-carbamic acid tert-butyl ester 
• 610316-27-3 [(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane 
• 205449-12-3 Methyl 2-azido-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-isopropylidene-L-xylonate 
• 205449-10-1 Methyl 5-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-L-xylonate 
• 205449-07-6 Methyl 5-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-L-lyxonate 
• 205449-09-8 Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester 
• 205449-18-9 (R)-Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester 

Downstream Products

• 205449-15-6 Benzyl 5-O-(aminocarbonyl)-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate 
• 22976-90-5 Polyoxin L 

Relevant academic research and scientific papers

The sulfinyl moiety as an internal nucleophile. Part 8: Efficient, stereospecific synthesis of (+)-polyoxamic acid

A straightforward and stereospecific synthesis of (+)-polyoxamic acid is disclosed. The key step of the synthesis involves the regio- and stereospecific bromohydration of an olefin via intramolecular participation by the sulfinyl group.

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.

Total syntheses of (-)-polyoxin J and (-)-polyoxin L

A convenient synthesis of the N-protected L-carbamoylpolyoxamic acid derivative (7) from 4-O-tert-butyldiphcnylsilyl-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.