180998-03-2

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 180998-04-3 ((2S,3R,4S,5R,6S)-6-Methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-diphenyl-phosphane 
• 20771-10-2 1-O-methyl-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranoside 
• 1101-41-3 Tetraphenyldiphosphin 

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.