127446-71-3

Basic information

• Product Name: Allyl 2,6-di-O-benzoyl-α-D-glucopyranoside
• Synonyms: Allyl 2,6-di-O-benzoyl-α-D-glucopyranoside
• CAS NO: 127446-71-3
• Molecular Weight: 428.439
• Mol File: 127446-71-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Allyl 2,6-di-O-benzoyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Allyl 2,6-di-O-benzoyl-α-D-glucopyranoside(127446-71-3)
• EPA Substance Registry System: Allyl 2,6-di-O-benzoyl-α-D-glucopyranoside(127446-71-3)

Safety Data

• Hazardous Substances Data: 127446-71-3(Hazardous Substances Data)

Upstream product

• 7464-56-4 1-O-allyl-α-D-glucopyranoside 
• 155896-88-1 Allyl 2-O-Benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 65987-12-4 1-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 98-88-4 benzoyl chloride 
• 48149-74-2 allyl D-glucopyranoside 
• 127446-68-8 Allyl 2-O-Benzoyl-α-D-glucopyranoside 

Downstream Products

• 127446-66-6 Allyl 2,6-Di-O-benzoyl-3,4-di-O-methylsulfonyl-α-D-glucopyranoside 
• 169822-05-3 2-dibenzyloxyphosphoryloxyethyl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside 
• 169822-00-8 allyl 2,6-di-O-benzyl-3,4-O-isopropylidene-α-D-glucopyranoside 
• 169822-04-2 (2-hydroxyethyl) 2,6-di-O-benzyl-α-D-glucopyranoside 
• 607364-84-1 allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside 
• 607364-85-2 allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-α-D-glucopyranoside 
• 607364-83-0 allyl 2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside 
• 227751-12-4 3',6'-di-O-acetyl-4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranose 1',2'-(allyl 2,6-di-O-benzoyl-α-D-glucopyranosid-3-yl orthoacetate) 
• 169822-01-9 allyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-α-D-glucopyranoside 

Relevant articles and documents

A Ca2+-mobilising carbohydrate-based polyphosphate: Synthesis of 2- hydroxyethyl α-D-glucopyranoside 2',3,4-trisphosphate

Two routes to a glucose-based mimic of the second messenger 1D-myo- inositol 1,4,5-trisphosphate related to adenophostin A are described. Fischer glycosidation of D-glucose with allyl alcohol in the presence of a strong cation-exchange resin gave a 7:3 α:β-anomeric mixture of allyl glucopyranosides (5ab) from which the pure α anomer 5a was isolated by crystallisation. Treatment of 5ab with 1.05 equiv of dibutyltin oxide followed by 2.1 equiv of benzoyl chloride gave allyl 2,6-di-O-benzoyl-α-D- glucopyranoside, which was converted in 3 steps into allyl 2,6-di-O-benzyl- 3,4-O-isopropylidene-α-D-glucopyranoside (4). Alternatively, treatment of 5a with 2.5 equiv of dibutyltin oxide followed by benzyl bromide gave allyl 2,6-di-O-benzyl-α-D-glucopyranoside (9) which was also converted into 4. Compound 4 was elaborated to the phosphorylation precursor 2-hydroxyethyl 2,6-di-O-benzyl-α-D-glucopyranoside (12) in a convenient one-pot reaction, and 12 was phosphorylated and deblocked to afford 2-hydroxyethyl α-D- glucopyranoside 2',3.4-trisphosphate. The 2,6-di-O-benzyl derivative 9 was converted in high yield into 2,6-di-O-benzyl-3,4-di-O-(p-methoxybenzyl)-D- glucopyranose, a useful intermediate for the synthesis of adenophostin A and related compounds.

Regioselective acylation of carbohydrates with 1-acyloxy-1H-benzotriazoles

Acylation of representative carbohydrate derivatives was accomplished with in situ generated 1-acyloxy-1H-benzotriazoles. The observed high regioselectivity, mild reaction conditions and convenient work-up make the presented one-pot procedure generally applicable and more advantageous than acylations with previously introduced reagents, including N-acylimidazoles.