23477-56-7

Basic information

• Product Name: methyl 4-O-benzyl-α-D-mannopyranoside
• Synonyms: methyl 4-O-benzyl-α-D-mannopyranoside
• CAS NO: 23477-56-7
• Molecular Weight: 284.309
• Mol File: 23477-56-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: methyl 4-O-benzyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-O-benzyl-α-D-mannopyranoside(23477-56-7)
• EPA Substance Registry System: methyl 4-O-benzyl-α-D-mannopyranoside(23477-56-7)

Safety Data

• Hazardous Substances Data: 23477-56-7(Hazardous Substances Data)

Upstream product

• 6748-91-0 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 134407-60-6 methyl 4-O-benzyl-2,3-di-O-p-methoxybenzyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 82185-79-3 methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 492-62-6 alpha-D-glucopyranose 
• 134407-59-3 (4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 498-07-7 levoglucosan 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 67-56-1 methanol 
• 22348-23-8 1,6-anhydro-4-O-benzyl-β-D-glucopyranose 

Downstream Products

• 134407-68-4 4-O-benzyl-1,5-anhydro-D-glucitol 
• 105265-51-8 1,2,3,6-tetra-O-acetyl-4-O-benzyl-α-D-mannopyranoside 
• 1414629-62-1 methyl 6-azido-6-deoxy-4-O-benzyl-2,3-di-O-trimethylsilyl-α-D-glucopyranoside 
• 134121-19-0 4-O-acetyl-1,5-anhydro-2,3,6-tri-O-(methoxycarbonylmethyl)-D-glucitol 
• 105265-52-9 2,3,6-tri-O-acetyl-4-O-benzyl-α-D-mannopyranosyl bromide 

Relevant articles and documents

Both d - And l -Glucose Polyphosphates Mimic d - myo-Inositol 1,4,5-Trisphosphate: New Synthetic Agonists and Partial Agonists at the Ins(1,4,5)P3Receptor

Chiral sugar derivatives are potential cyclitol surrogates of the Ca2+-mobilizing intracellular messenger d-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P3]. Six novel polyphosphorylated analogues derived from both d- and l-glucose were synthesized. Binding to Ins(1,4,5)P3 receptors [Ins(1,4,5)P3R] and the ability to release Ca2+ from intracellular stores via type 1 Ins(1,4,5)P3Rs were investigated. β-d-Glucopyranosyl 1,3,4-tris-phosphate, with similar phosphate regiochemistry and stereochemistry to Ins(1,4,5)P3, and α-d-glucopyranosyl 1,3,4-tris-phosphate are full agonists, being equipotent and 23-fold less potent than Ins(1,4,5)P3, respectively, in Ca2+-release assays and similar to Ins(1,4,5)P3 and 15-fold weaker in binding assays. They can be viewed as truncated analogues of adenophostin A and refine understanding of structure-activity relationships for this Ins(1,4,5)P3R agonist. l-Glucose-derived ligands, methyl α-l-glucopyranoside 2,3,6-trisphosphate and methyl α-l-glucopyranoside 2,4,6-trisphosphate, are also active, while their corresponding d-enantiomers, methyl α-d-glucopyranoside 2,3,6-trisphosphate and methyl α-d-glucopyranoside 2,4,6-trisphosphate, are inactive. Interestingly, both l-glucose-derived ligands are partial agonists: they are among the least efficacious agonists of Ins(1,4,5)P3R yet identified, providing new leads for antagonist development.

Regioselectivity of tin-mediated benzylation of glycoside

Regioselectivity of methyl α-D-glucopyranoside benzylation using dibutyltin dimethoxide (DBDM) as stannylating agent was probed, general factors affecting regioselectivity have been examined. The results show the O-2 position of glucoside has advantage of

A novel method for regioselective ring-opening reduction of 4,6-O-benzylidene hexopyranoside derivatives using CoCl2 and BH3·THF

A novel and facile reductive ring-opening reaction for 4,6-O-benzylidene acetal derivatives of hexopyranosides using CoCl2/BH3·THF gave the corresponding 4-O-benzyl-6-OH derivatives selectively in good yields. This convenient method