169822-01-9

Basic information

• Product Name: allyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-α-D-glucopyranoside
• Synonyms: allyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-α-D-glucopyranoside
• CAS NO: 169822-01-9
• Molecular Weight: 468.504
• Mol File: 169822-01-9.mol

Chemical Properties

• CAS DataBase Reference: allyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-α-D-glucopyranoside(169822-01-9)
• EPA Substance Registry System: allyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-α-D-glucopyranoside(169822-01-9)

Safety Data

• Hazardous Substances Data: 169822-01-9(Hazardous Substances Data)

Upstream product

• 48149-74-2 allyl D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 116-11-0 2-Methoxypropene 
• 127446-71-3 Allyl 2,6-di-O-benzoyl-α-D-glucopyranoside 

Downstream Products

• 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 

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.

(2-hydroxyethyl)-α-D-glucopyranoside-2',3,4-trisphosphate: Synthesis of a second messenger mimic related to adenophostin A

A concise synthetic route from D-glucose to a chiral, biologically active, phosphorylated analogue of the highly potent Ca2+-mobilising agonist adenophostin A has been developed, involving a regioselective dibenzylation of allyl α-D-glucopyranoside and a one-pot Lemieux-type allyl oxidation with subsequent reduction and neighbouring deketalisation, to provide the key intermediate for phosphorylation.