3162-96-7

Basic information

• Product Name: METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: METHYL 4,6-O-BENZILIDINE-D-GLUCOPYRANOSIDE;METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE;METHYL 4,6-O-BENZYLIDENE-A-D-GLUCOPYRANOSIDE;(+)-(4,6-O-BENZYLIDENE)METHYL-ALPHA-D-GLUCOPYRANOSIDE;4,6-O-BENZYLIDENE-METHYL-ALPHA-D-GLUCOPYRANOSIDE;4,6-BENZYLIDENE-ALPHA-METHYL-D-GLUCOSIDE;4,6-BENZYLIDENE-A-METHYL-D-GLUCOSIDE;2,3-Dibenzyl-4,6-Ethylidine Glucopyranose
• CAS NO: 3162-96-7
• Molecular Formula: C14H18O6
• Molecular Weight: 282.29
• EINECS: 221-615-2
• Product Categories: Sugars, Carbohydrates & Glucosides;13C & 2H Sugars;Biochemistry;Glucose;Glycosides;O-Substituted Sugars;Sugars;Carbohydrates & Derivatives
• Mol File: 3162-96-7.mol
• Article Data: 193

Chemical Properties

• Melting Point: 164-167 °C
• Boiling Point: 384.9°C (rough estimate)
• Flash Point: 239.8 °C
• Appearance: White crystalline solid
• Density: 1.2640 (rough estimate)
• Vapor Pressure: 9.45E-10mmHg at 25°C
• Refractive Index: 105 ° (C=2, MeOH)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, DMF, DMSO, Ethyl Acetate, Methanol
• PKA: 12.79±0.70(Predicted)
• Water Solubility: It is soluble in water, acetone, benzene, ethyl ether
• Sensitive: Hygroscopic
• BRN: 1291458
• CAS DataBase Reference: METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE(3162-96-7)
• EPA Substance Registry System: METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE(3162-96-7)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 22-24/25-45-36/37/39-27-26
• WGK Germany: 3
• F: 21
• Hazardous Substances Data: 3162-96-7(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 3162-96-7 differently. You can refer to the following data:
1. Methyl 4,6-O-Benzylidene-α-D-glucopyranoside is a derivative of methyl α-D-glucopyranoside tested for in vitro antibacterial activity.
2. Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside, is used as a chiral building block and important intermediate in the preparation of different sugars. It is also used as an intermediate in chemical, pharmaceutical intermediate, pharmaceutical research and reagent.

InChI:InChI=1/C14H18O6/c1-17-14-11(16)10(15)12-9(19-14)7-18-13(20-12)8-5-3-2-4-6-8/h2-6,9-16H,7H2,1H3/t9-,10-,11-,12-,13-,14+/m0/s1

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 64552-05-2 (2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 100-52-7 benzaldehyde 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 
• 2774-22-3 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 67-56-1 methanol 
• 1202385-04-3 C₂₃H₃₀O₁₀ 
• 51223-62-2 methyl β-D-galactopyranoside 
• 2774-22-3 2,3-O-diacetyl-(4,6-O-benzylidene)methyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 1769-06-8 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-mannopyranoside 

Downstream Products

• 74984-87-5 Methyl-4,5-O-benzyliden-2,3-carbonato-α-D-mannopyranosid 
• 120200-50-2 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-mannopyranoside 
• 2872-56-2 methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 2774-22-3 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside 
• 2774-23-4 methyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 123977-22-0 methyl 4,6-O-benzylidene-2,3-di-O-(2'-methylacrolyl)-α-D-glucopyranoside 
• 70774-92-4 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside 
• 102380-64-3 methyl-[O²,O³-bis-benzenesulfinyl-O⁴,O⁶-((R)-benzylidene)-α-D-glucopyranoside] 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 6748-85-2 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 73705-90-5 methyl-[O⁴,O⁶-((R)-benzylidene)-O²,O³-bis-phenylcarbamoyl-α-D-glucopyranoside] 
• 80244-98-0 methyl-[O⁴,O⁶-((R)-benzylidene)-O²,O³-bis-(4-nitro-benzoyl)-α-D-glucopyranoside] 
• 139893-71-3 methyl 4,6-O-benzylidene-α-D-glucopyranoside 2-O-methanesulfonate 
• 65530-21-4 methyl 4,6-O-benzylidene-2,3-di-O-methanesulfonyl-α-D-glucopyranoside 

Relevant articles and documents

Facile Cleavage of Benzyl Ethers by Catalytic Transfer Hydrogenation

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Cu-free Sonogashira Type Cross-Coupling of 6-Halo-2-cyclopropyl-3-(pyridyl-3-ylmethyl) Quinazolin-4(3H)-ones as Potential Antimicrobial Agents

C(sp)–C(sp2) bond formation via Sonogashira cross-coupling reactions on 6-halo-2-cyclopropyl-3-(pyridyl-3-ylmethyl)quinazolin-4(3H)-ones with appropriate alkynes was explored. Optimization of reaction conditions with various catalysts, ligands, bases, and solvents was conducted. The combination of PdCl2(MeCN)2 with X-Phos proved to be the best metal–ligand system for this conversion in the presence of triethylamine (Et3N) in tetrahydrofuran at room temperature for iodosubstrates, at 80°C for the bromosubstrates in 8?h, and also for the chlorosubstrates in 16?h. We also demonstrated synthesis of a successful diversity-oriented synthesis library of highly functionalized quinazolinones via Cu-free Sonogashira coupling of diverse aryl halides and azido-alkyne (“click”) ligation reactions with substituted azides. The library exhibited significant antimicrobial activity when screened against several microorganisms.

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.

Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides

A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is

Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts

Herein, we report the oligopeptide-catalyzed site-selective acylation of partially protected monosaccharides. We identified catalysts that invert site-selectivity compared to N-methylimidazole, which was used to determine the intrinsic reactivity, for 4,6