129001-58-7

Upstream product

• 545-06-2 trichloroacetonitrile 
• 132592-33-7 tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 120312-07-4 tert-butyldimethylsilyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 120312-08-5 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 120312-09-6 tert-Butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid 
• 99049-68-0 tert-Butyldimethylsilyl-2-azido-2-desoxy-4,6-O-isopropyliden-β-D-glucopyranosid 

Downstream Products

• 95975-85-2 bulgecin C 
• 129001-57-6 (2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester) 
• 132592-39-3 (2S,4S,5R)-4-<(2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester) 
• 132696-23-2 (2S,4S,5R)-4-<(2-acetamido-4-O-sulfo-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester) 
• 132621-15-9 N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester) 
• 132592-38-2 (2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester 
• 132592-37-1 (2S,4S,5R)-4-<(2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester 
• 132621-14-8 N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester) 

Relevant academic research and scientific papers

Electrochemical Oxidation of Proline Derivatives: Total Syntheses of Bulgecinine and Bulgecin C

The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented.Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) ester (19).The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent.Bulgecin C (1c) was prepared via a β-stereoselective glycosidation reaction using a 2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.