148926-05-0

Basic information

• Product Name: methyl 3,4,6-tri-O-benzyl-2-O-methyl-α-D-glucopyranoside
• Synonyms: methyl 3,4,6-tri-O-benzyl-2-O-methyl-α-D-glucopyranoside
• CAS NO: 148926-05-0
• Molecular Weight: 478.585
• Mol File: 148926-05-0.mol

Chemical Properties

• CAS DataBase Reference: methyl 3,4,6-tri-O-benzyl-2-O-methyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3,4,6-tri-O-benzyl-2-O-methyl-α-D-glucopyranoside(148926-05-0)
• EPA Substance Registry System: methyl 3,4,6-tri-O-benzyl-2-O-methyl-α-D-glucopyranoside(148926-05-0)

Safety Data

• Hazardous Substances Data: 148926-05-0(Hazardous Substances Data)

Upstream product

• 20672-67-7 (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol 
• 74-88-4 methyl iodide 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 20672-67-7 (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol 

Relevant articles and documents

Triisobutylaluminium and dusobutylaluminium hydride as molecular scalpels: The regioselective stripping of perbenzylated sugars and cyclodextrins

To explain the remarkable regioselective de-O-benzylating properties of diisobutylaluminium hydride (DIBAL-H) and triisobutylaluminium (TIBAL) towards polybenzylated sugars or cyclodextrins, we propose a plausible mechanistic rationale critically involving the kinetic formation of a product-generating 2:1 Al-benzylated sugar complex. For the reaction to occur, one pair of adjacent oxygen atoms should first be able to form a chelation complex with the first equivalent of aluminium reagent, either a highly fluxional complex with tetracoordinate aluminium species or a pentacoordinate one. The second equivalent then induces the regioselectivity of the de-O-alkylation by coordinating preferentially to one of the oxygen atoms of the selected pair.