86420-71-5

Basic information

• Product Name: methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside
• Synonyms: methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside
• CAS NO: 86420-71-5
• Molecular Weight: 386.401
• Mol File: 86420-71-5.mol

Chemical Properties

• CAS DataBase Reference: methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside(86420-71-5)
• EPA Substance Registry System: methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside(86420-71-5)

Safety Data

• Hazardous Substances Data: 86420-71-5(Hazardous Substances Data)

Upstream product

• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 71117-41-4 methyl 4,6-O-benzylidene-α-D-altropyranoside 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 93-97-0 benzoic acid anhydride 
• 65-85-0 benzoic acid 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 1202384-89-1 C₂₃H₂₄O₉ 
• 91685-05-1 methyl 3-O-benzoyl-4, 6-O-benzylidene-α-D-mannopyranoside 

Downstream Products

• 94968-55-5 Methyl-3,4-di-O-benzoyl-α-D-glucopyranosid 
• 80245-05-2 methyl 3,6-di-O-benzoyl-α-D-glucopyranoside 
• 1313374-89-8 methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->2)-3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 1313374-88-7 methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 80245-04-1 methyl 3,4,6-tri-O-benzoyl-α-D-glucopyranoside 
• 1313374-91-2 methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-glucopyranoside 
• 1313374-90-1 methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-glucopyranoside 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 6748-85-2 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 21056-54-2 methyl 3-O-benzoyl-α-D-glucopyranoside 
• 142967-83-7 methyl O-(2,4-di-O-benzoyl-3-O-bromoacetyl-α-L-rhamnopyranosyl)-(1-3)-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1-2)-4,6-O-benzylidene-3-O-benzoyl-α-D-galactopyranoside 
• 142967-84-8 methyl O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1-3)-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1-2)-4,6-O-benzylidene-3-O-benzoyl-α-D-galactopyranoside 
• 142967-79-1 methyl O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1-2)-4,6-O-benzylidene-3-O-benzoyl-α-D-galactopyranoside 
• 142967-78-0 methyl O-(2,4-di-O-benzoyl-3-O-bromoacetyl-α-L-rhamnopyranosyl)-(1-2)-4,6-O-benzylidene-3-O-benzoyl-α-D-galactopyranoside 

Relevant articles and documents

SnCl2-Catalyzed Acetalation/Selective Benzoylation Sequence for the Synthesis of Orthogonally Protected Glycosyl Acceptors

Based on SnCl2-catalyzed acetalation and selective benzoylation, a one-pot strategy to efficiently synthesize orthogonally protected glycosyl acceptors with 2-OH/3-OH was developed. Consequently, 2-OBz or 3-OBz 4,6-O-benzylidene galactosides and glucosides were efficiently prepared in moderate to high yields starting from free galactosides and glucosides, and were used as valuable glycosyl acceptors for the synthesis of blood group antigens O and B analogues in this study.

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Highly Regioselective Monoacylation of Unprotected Glucopyranoside Using Transient Directing-Protecting Groups

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Regioselective Benzoylation of 4,6-O-Benzylidene Acetals of Glycopyranosides in the Presence of Transition Metals

Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides by benzoic anhydride in acetonitrile in the presence of Cu(CF3COO)2 as a promoter gave 2-benzoates for α-D-glucopyranosides and α-D-mannopyranosides and 3-benzoates for β-D-galactopyranosides in good yields with high regioselectivity. Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides of D-galactose and D-mannose by benzoyl chloride in the presence of MoO2(acac)2 as a catalyst in all studied cases led to regioselective 3-substitution.

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