51016-18-3

Upstream product

• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 203061-84-1 methyl 4,6-O-benzylidene-2-O-methanesulfonyl-3-O-(2-methoxyethoxymethyl)-α-D-glucopyranoside 
• 203061-72-7 Benzoic acid (2S,3R,4S,5R,6S)-2-acetylsulfanylmethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methanesulfonyloxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 203061-70-5 Benzoic acid (2S,3R,4S,5R,6S)-2-bromomethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methanesulfonyloxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 203061-74-9 Benzoic acid (2S,3R,4S,5R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-2-mercaptomethyl-5-methanesulfonyloxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 203061-77-2 Benzoic acid (2R,3R,4S,5R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-5-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 203061-86-3 methyl 6-S-acetyl-4-O-benzoyl-2-O-methanesulfonyl-3-O-(2-methoxyethoxymethyl)-6-thio-α-D-glucopyranoside 
• 203061-85-2 methyl 4-O-benzoyl-6-bromo-6-deoxy-2-O-methanesulfonyl-3-O-(2-methoxyethoxymethyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Action of base on methyl 6-thio-(and 6-deoxy-) 2-O-methanesulfonyl-α-D-glucopyranoside derivatives

Treatment of methyl 4-O-benzoyl-3 -O-tert-butyldiphenylsilyl-2-O-methanesulfonyl-6-thio-α-D-glucopyranoside (8) and its 6-deoxy analogue (11) with methanolic sodium methoxide, afforded methyl 2,3-anhydro-mannopyranoside derivatives as a consequence of an O3 → O4 TBDPS rearrangement. When the protecting group at C-3 was 2-methoxyethoxy methyl ether only deacylation and methanolysis of the methanesulfonyl group occurred.