22875-28-1

Upstream product

• 180998-03-2 Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester 

Downstream Products

• 1222854-41-2 1-O-methyl-6-O-[(3S)-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoyl]-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranose 
• 1222854-62-7 1-O-methyl-6-O-[(3R)-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoyl]-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranose 
• 1373313-60-0 C₂₉H₅₁NO₈Si₃ 
• 1373313-57-5 C₂₄H₄₂O₈Si₃ 
• 142886-50-8 methyl 6-O-(p-coumaroyl)-β-D-galactopyranoside 
• 142886-51-9 methyl 6-O-feruloyl-β-D-galactopyranoside 
• 142886-48-4 methyl 6-O-(4'-O-acetyl-p-coumaroyl)-β-D-galactopyranoside 
• 142886-49-5 methyl 6-O-(4'-O-acetylferuloyl)-β-D-galactopyranoside 
• 142886-52-0 methyl 2,3,4-tri-O-acetyl-6-O-(4'-O-acetyl-p-coumaroyl)-β-D-galactopyranoside 
• 142886-53-1 methyl 2,3,4-tri-O-acetyl-6-O-(4'-O-acetylferuloyl)-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of Methyl 6-Deoxy-6-diphenylphosphino-α-D-glucopyranoside: Temperature-Dependence of the Primary O-Tosyl Cleavage Mode

Methyl α-D-glucopyranoside is converted to methyl 6-p-toluenesulfonyl-2,3,4-tris-O-trimethylsilyl-α-D-glucopyranoside 2 and then reacted with lithium diphenylphosphide in THF. When the reaction is carried out at room temperature and below, S-O cleavage dominates giving methyl 2,3,4-tris-O-trimethylsilyl-α-D-glucopyranoside 3, whereas at 60°C in THF or at 35°C in diethyl ether, C-O cleavage occurs yielding the title carbohydrate-phosphine 4 in good yield after deprotection.