129264-68-2

Basic information

• Product Name: (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) 3,4,6-tri-O-benzyl-1-(2,2,6,6-tetramethyl-1-piperidinyl)-β-D-fructofuranoside
• Synonyms: (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) 3,4,6-tri-O-benzyl-1-(2,2,6,6-tetramethyl-1-piperidinyl)-β-D-fructofuranoside
• CAS NO: 129264-68-2
• Molecular Weight: 1112.41
• Mol File: 129264-68-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) 3,4,6-tri-O-benzyl-1-(2,2,6,6-tetramethyl-1-piperidinyl)-β-D-fructofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) 3,4,6-tri-O-benzyl-1-(2,2,6,6-tetramethyl-1-piperidinyl)-β-D-fructofuranoside(129264-68-2)
• EPA Substance Registry System: (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) 3,4,6-tri-O-benzyl-1-(2,2,6,6-tetramethyl-1-piperidinyl)-β-D-fructofuranoside(129264-68-2)

Safety Data

• Hazardous Substances Data: 129264-68-2(Hazardous Substances Data)

Upstream product

• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 129264-67-1 3,4,6-tri-O-benzyl-1-deoxy-1-iodo-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-β-D-fructofuranoside 

Downstream Products

• 57-50-1 Sucrose 
• 126-14-7 sucrose octaacetate 

Relevant articles and documents

Redox glycosidation: the use of Nozaki-Takai methylenylation in a highly stereoselective synthesis of sucrose

Sequential reaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose (7) with butyllithium and 2-thio-3-nitropyridine (6) at -78 deg C gave 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 2,3,5-tri-O-benzyl-4-O-(tert-butyldiphenylsilyl)-D-arabinonate (8: 71percent, α:β > 50:1).Ester carbonyl methylenylation, desilylation, and iodoetherification in the presence of silica gave 3,4,6-tri-O-benzyl-1-deoxy-1-iodo-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-fructofuranoside (15: 44percent, α:β > 50:1).This neopentylic iodide 15 was converted into sucrose (1: 80percent) by free-radical substitution using TEMPO (24) followed by sodium-ammonia reduction, acetylation and Zemplen methanolysis.