203061-85-2

Upstream product

• 203061-84-1 methyl 4,6-O-benzylidene-2-O-methanesulfonyl-3-O-(2-methoxyethoxymethyl)-α-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 51016-18-3 methyl 4,6-O-benzylidene-2-O-methanesulfonyl-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.