177723-45-4

Upstream product

• 186581-53-3 diazomethane 
• 100-39-0 benzyl bromide 
• 177723-40-9 ethyl 6-azido-2,3,6-trideoxy-α-D-erythro-hexopyranoside 
• 177723-44-3 (4S,5R)-5-acetoxy-6-azido-4-(phenylmethoxy) hexanal 
• 135103-81-0 ethyl 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-α-D-erythro-hexopyranoside 
• 177723-39-6 ethyl 6-O-tosyl-2,3-dideoxy-α-D-erythro-pyranoside 
• 135103-82-1 6-azido-2,3,6-trideoxy-4-O-(phenylmethyl)-D-erythro-hexose-(propane-1,3-diyl)dithioacetal 
• 177723-43-2 6-azido-2,3,6-trideoxy-5-acetoxy-4-O-(phenylmethyl)-D-erythro-hexose-(propane-1,3-diyl)dithioacetal 
• 23339-16-4 (2R,3S,6S)-6-ethoxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-ol 

Downstream Products

• 135103-84-3 methyl(4S)4-benzyloxy-4-<(2S)-N-Boc-aziridin-2-yl>-butanoate 
• 135103-80-9 N-Boc-O-benzyl-(4S,5S)-5-amino-4-hydroxy-6-phenylhexanoic acid methyl ester 
• 135103-85-4 N-Boc-O-Benzyl-(4S,5S)-5-amino-4-hydroxy-6-phenylhexanoic acid 
• 135103-83-2 methyl (4S,5R)-6-azido-5-hydroxy-4-(phenylmethoxy) hexanoate 

Relevant academic research and scientific papers

Stereoselective synthesis of hydroxyethylene dipeptide isostere from sugar

Regioselective opening of the aziridine ring in the carbohydrate-based precursor led to the stereoselective synthesis of N-Boc-O-benzyl-(4S,5S)-5-amino-4-hydroxy-6-phenylhexanoic acid methyl ester, the hydroxyethylene dipeptide isostere moiety of potent HIV-1 protease inhibitor.

STEREOSELECTIVE SYNTHESIS OF N-BOC-O-BENZYL-(4S,5S)-5-AMINO-4-HYDROXY-6-PHENYLHEXANOIC ACID, THE HYDROXYETHYLENE ISOSTERIC MOIETY OF POTENT HIV-1 PROTEASE INHIBITOR

N-Boc-O-benzyl-(4S,5S)-5-amino-4-hydroxy-6-phenylhexanoic acid is synthesized in a highly stereoselective way involving, as a key step, regioselective opening of carbohydrate-based aziridine ring.