33535-04-5

Basic information

• Product Name: METHYL-3-O-BENZOYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: METHYL-3-O-BENZOYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE
• CAS NO: 33535-04-5
• Molecular Formula: C₂₁H₂₂O₇
• Molecular Weight: 386.39518
• Mol File: 33535-04-5.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL-3-O-BENZOYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-3-O-BENZOYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE(33535-04-5)
• EPA Substance Registry System: METHYL-3-O-BENZOYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE(33535-04-5)

Safety Data

• Hazardous Substances Data: 33535-04-5(Hazardous Substances Data)

Upstream product

• 110-86-1 pyridine 
• 98-88-4 benzoyl chloride 
• 18031-56-6 methyl-[O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside] 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 67-64-1 acetone 
• 389-04-8 methyl-[O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside] 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 147514-07-6 Methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 71117-41-4 methyl 4,6-O-benzylidene-α-D-altropyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 93-97-0 benzoic acid anhydride 
• 4148-58-7 (4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 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 
• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 110715-29-2 methyl 4,6-O-benzylidene-2-O-methyl-α-D-glucopyranoside 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 
• 73159-22-5 methyl 3-O-acetyl-4,6-O-benzylidene-2-chloro-2-deoxy-α-D-mannopyranoside 
• 35775-02-1 methyl 4,6-O-benzylidene-2-chloro-2-deoxy-α-D-mannopyranoside 
• 6748-85-2 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside 

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.

DBN-Catalyzed Regioselective Acylation of Carbohydrates and Diols in Ethyl Acetate

The 1,5-diazabicyclo[4.3.0]non-5-ene (DBN)-catalyzed regioselective acylation of carbohydrates and diols in ethyl acetate has been developed. The hydroxyl groups can be selectively acylated by the corresponding anhydride in EtOAc in the presence of a catalytic amount (as low as 0.1 equiv.) of DBN at room temperature to 40 °C. This method avoids metal catalysts and toxic solvents, which makes it comparatively green and mild, and it uses less organic base compared with other selective acylation methods. Mechanism studies indicated that DBN could catalyze the selective acylation of hydroxyl moieties through a dual H-bonding interaction.

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

The regioselective functionalization of monosaccharides is notoriously achieved using metal catalysis, lengthy synthetic strategies requiring protection/deprotection, various enzymes, or other methods that target cis-diols (and thus cannot be used with glucopyranose derivatives), In this paper, we report a new method using selected boronic acids as temporary protecting groups, and describe its application to the regioselective functionalization of methyl α-d-glucopyranoside, the most difficult monosaccharide to functionalize regioselectively. Generally, reactions of glucopyranosides may lead to a plethora of mono- and polyfunctionalized derivatives, yet our method gave the 3-O-acetylated, 2-O-benzoylated, and 2-O-pivaloylated derivatives of methyl α-d-glucopyranoside as major products. We focused on the use of recyclable and green temporary protecting groups (in a one-pot reaction) and on the modulation of the intramolecular hydrogen-bonding network using selected arylboronic acids. A complete scalable procedure leading to a single regioisomer from unprotected methyl α-d-glucopyranoside is presented.