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

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

Uses

Used in Pharmaceutical Industry:
METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE is used as a chiral building block and an important intermediate for the preparation of different sugars. Its unique structure allows it to be a key component in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapies.
Used in Chemical Industry:
In the chemical industry, METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE serves as an intermediate in the synthesis of various chemical products. Its versatile structure makes it a valuable asset in the development of new chemical compounds and materials.
Used in Research and Development:
METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE is also used as a reagent in pharmaceutical research and development. Its unique properties make it an essential tool for scientists and researchers working on the discovery and development of new drugs and chemical compounds.
Used in Antibacterial Applications:
METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE has been tested for in vitro antibacterial activity, making it a potential candidate for the development of new antibacterial agents. Its effectiveness against various bacterial strains could lead to the creation of novel treatments for bacterial infections.

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 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 208921-46-4 methyl-[O⁴,O⁶((R)-benzylidene-O³-nitro-α-D-glucopyranoside] 
• 5115-95-7 methyl-[O⁴,O⁶-((R)-benzylidene-O²,O³-dinitro-α-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 
• 492-62-6 alpha-D-glucopyranose 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 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 
• 70774-92-4 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside 
• 2280-44-6 D-Glucose 

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 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 98392-36-0 Methyl 2-O-acetyl-4,6-O-(phenylmethylene)-α-D-mannopyranoside 
• 2872-56-2 3-O-acetyl-(4,6-O-benzylidene)methyl-α-D-mannopyranoside 
• 144490-59-5 methyl 4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-mannopyranoside 
• 2774-22-3 2,3-O-diacetyl-(4,6-O-benzylidene)methyl-α-D-mannopyranoside 
• 2774-19-8 (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 82877-79-0 methyl 4,6-O-benzylidene-2-O-(N,N-diethylcarbamoyl)-α-D-mannoside 
• 82039-66-5 methyl 4,6-O-benzylidene-2-O-(N,N-dimethylcarbamoyl)-α-D-mannoside 
• 120200-51-3 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 117677-64-2 methyl 4,6-O-benzylidene-2,3-O-bis(diphenylphosphino)-α-D-mannopyranoside 
• 91102-84-0 (+)-1,7-Bis(methyl-4,6-O-benzyliden-3-desoxy-α-D-mannopyranosido)-1,4,7-trioxaheptan 
• 67077-31-0 (+)-Bis(methyl-4,6-O-benzyliden-2,3-didesoxy-α-D-mannopyranosido)<2,3-b:3',2'-k>-1,4,7,10,13,16-hexaoxacyclooctadecan 

Relevant articles and documents

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.

Epoxy functionalized polymethacrylates based on various multifunctional D-glucopyranoside acetals

The synthesis of acetal-derived d-glucopyranosides with a various number of hydroxyl groups (the first step, acetalization) and their modified forms with bromoester groups (the second step, esterification) are presented here. The latter, due to the type o

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.

Carbohydrate-Derived Metal-Chelator-Triggered Lipids for Liposomal Drug Delivery

Liposomes are versatile three-dimensional, biomaterial-based frameworks that can spatially enclose a variety of organic and inorganic biomaterials for advanced targeted-delivery applications. Implementation of external-stimuli-controlled release of their cargo will significantly augment their wide application for liposomal drug delivery. This paper presents the synthesis of a carbohydrate-derived lipid, capable of changing its conformation depending on the presence of Zn2+: an active state in the presence of Zn2+ ions and back to an inactive state in the absence of Zn2+ or when exposed to Na2EDTA, a metal chelator with high affinity for Zn2+ ions. This is the first report of a lipid triggered by the presence of a metal chelator. Total internal reflection fluorescence microscopy and a single-liposome study showed that it indeed was possible for the lipid to be incorporated into the bilayer of stable liposomes that remained leakage-free for the fluorescent cargo of the liposomes. On addition of EDTA to the liposomes, their fluorescent cargo could be released as a result of the membrane-incorporated lipids undergoing a conformational change.

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

Me3SI-promoted chemoselective deacetylation: a general and mild protocol

A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.

Sweet Drugs for Bad Bugs: A Glycomimetic Strategy against the DC-SIGN-Mediated Dissemination of SARS-CoV-2

The C-type lectin receptor DC-SIGN is a pattern recognition receptor expressed on macrophages and dendritic cells. It has been identified as a promiscuous entry receptor for many pathogens, including epidemic and pandemic viruses such as SARS-CoV-2, Ebola virus, and HIV-1. In the context of the recent SARS-CoV-2 pandemic, DC-SIGN-mediated virus dissemination and stimulation of innate immune responses has been implicated as a potential factor in the development of severe COVID-19. Inhibition of virus binding to DC-SIGN, thus, represents an attractive host-directed strategy to attenuate overshooting innate immune responses and prevent the progression of the disease. In this study, we report on the discovery of a new class of potent glycomimetic DC-SIGN antagonists from a focused library of triazole-based mannose analogues. Structure-based optimization of an initial screening hit yielded a glycomimetic ligand with a more than 100-fold improved binding affinity compared to methyl α-d-mannopyranoside. Analysis of binding thermodynamics revealed an enthalpy-driven improvement of binding affinity that was enabled by hydrophobic interactions with a loop region adjacent to the binding site and displacement of a conserved water molecule. The identified ligand was employed for the synthesis of multivalent glycopolymers that were able to inhibit SARS-CoV-2 spike glycoprotein binding to DC-SIGN-expressing cells, as well as DC-SIGN-mediated trans-infection of ACE2+ cells by SARS-CoV-2 spike protein-expressing viruses, in nanomolar concentrations. The identified glycomimetic ligands reported here open promising perspectives for the development of highly potent and fully selective DC-SIGN-targeted therapeutics for a broad spectrum of viral infections.

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

Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides

A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, respectively.

Acceleration and deceleration factors on the hydrolysis reaction of 4,6-O-benzylidene acetal group

The benzylidene acetal group is one of the most important protecting groups not only in carbohydrate chemistry but also in general organic chemistry. In the case of 4,6-O-benzylidene glycosides, we previously found that the stereochemistry at 4-position altered the reaction rate constant for hydrolysis of benzylidene acetal group. However, a detail of the acceleration or deceleration factor was still unclear. In this work, the hydrolysis reaction of benzylidene acetal group was analyzed using the Arrhenius and Eyring plot to obtain individual parameters for glucosides (Glc), mannosides (Man), and galactosides (Gal). The Arrhenius and Eyring plot indicated that the pre-exponential factor (A) and ΔS? were critical for the smallest reaction rate constant of Gal among nonacetylated substrates. On the other hand, both Ea/ΔH? and A/ΔS? were influential for the smallest reaction rate constant of Gal among diacetylated substrates. All parameters obtained suggested that the rate constant for hydrolysis reaction was regulated by protonation and hydration steps along with solvation. The obtained parameters support wide use of benzylidene acetal group as orthogonal protection of cis- and trans-fused bicyclic systems through the fast hydrolysis of the trans-fused benzylidene acetal group.