17791-37-6

Basic information

• Product Name: Methyl 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranoside
• Synonyms: Methyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside;Methyl 2,3,4,6-Tetrakis-O-(phenylMethyl)-α-D-glucopyranoside;Methyl Tetra-O-benzyl-α-D-glucopyranoside
• CAS NO: 17791-37-6
• Molecular Formula: C₃₅H₃₈O₆
• Molecular Weight: 554.67
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 17791-37-6.mol
• Article Data: 135

Chemical Properties

• Melting Point: 26-27°C
• Boiling Point: 656.9 °C at 760 mmHg
• Flash Point: 248 °C
• Appearance: yellow thick oil
• Density: 1.18 g/cm³
• Vapor Pressure: 2.11E-16mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: Refrigerator
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Methyl 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranoside(17791-37-6)
• EPA Substance Registry System: Methyl 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranoside(17791-37-6)

Safety Data

• Hazardous Substances Data: 17791-37-6(Hazardous Substances Data)

Usage

Description

Methyl 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranoside is a synthetic compound derived from α-D-glucopyranoside, a type of sugar molecule. It is characterized by its yellow thick oil appearance and is primarily used in organic synthesis for various applications.

Uses

Used in Organic Synthesis:
Methyl 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranoside is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows for the creation of a wide range of molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranoside is used as a key building block for the synthesis of complex carbohydrate-based drugs. Its ability to form various derivatives makes it a valuable asset in the development of new therapeutic agents.
Used in Chemical Research:
Methyl 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranoside is also utilized in chemical research as a model compound for studying the properties and reactivity of sugar molecules. This helps researchers gain a better understanding of the fundamental chemistry involved in carbohydrate-based reactions and interactions.
Used in Material Science:
In the field of material science, Methyl 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranoside can be used as a component in the development of novel materials with specific properties. Its unique structure and reactivity make it a promising candidate for creating materials with tailored characteristics for various applications.

InChI:InChI=1/C35H38O6/c1-36-35-34(40-25-30-20-12-5-13-21-30)33(39-24-29-18-10-4-11-19-29)32(38-23-28-16-8-3-9-17-28)31(41-35)26-37-22-27-14-6-2-7-15-27/h2-21,31-35H,22-26H2,1H3

Upstream product

• 67-56-1 methanol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 100-44-7 benzyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 96863-21-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate 
• 104992-64-5 methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 329365-86-8 ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide 
• 872123-62-1 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranoside 
• 367947-05-5 2,6-dinitro-4-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 530114-05-7 2,3,4,6-tetra-O-benzyl-1-O-(N-allylthiocarbamoyl)-β-D-glucopyranose 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 91510-87-1 2-methyl-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propene 
• 91510-87-1 2-methyl-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propene 
• 92413-81-5 3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)butene 
• 92413-82-6 2-bromo-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propene 
• 91602-61-8 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 65556-30-1 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 3866-62-4 2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose 
• 117639-25-5 methyl 6-O-acetate-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 82659-59-4 3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene 
• 194410-25-8 9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 

Relevant articles and documents

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.

Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors

We have designed unprecedented cholinesterase inhibitors based on 1-deoxynojirimycin as potential anti-Alzheimer’s agents. Compounds are comprised of three key structural motifs: the iminosugar, for interaction with cholinesterase catalytic anionic site (

Design, synthesis, and biological evaluation of desmuramyl dipeptides modified by adamantyl-1,2,3-triazole

Muramyl dipeptide (MDP) is the smallest peptidoglycan fragment able to trigger the immune response. Structural modification of MDP can lead to the preparation of analogs with improved immunostimulant properties, including desmuramyl peptides (DMPs). The aim of this work was to prepare the desmuramyl peptide (L-Ala-D-Glu)-containing adamantyl-triazole moiety and its mannosylated derivative in order to study their immunomodulatory activities in vivo. The adjuvant activity of the prepared compounds was evaluated in a murine model using ovalbumin as an antigen, and compared to the reference adjuvant ManAdDMP. The results showed that the introduction of the lipophilic adamantyl-triazole moiety at the C-terminus of L-Ala-D-Glu contributes to the immunostimulant activity of DMP, and that mannosylation of DMP modified with adamantyl-triazole causes the amplification of its immunostimulant activity.