83462-67-3

Basic information

• Product Name: METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE
• Synonyms: METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE
• CAS NO: 83462-67-3
• Molecular Formula: C₃₅H₃₈O₆
• Molecular Weight: 554.67262
• Product Categories: Carbohydrates & Derivatives
• Mol File: 83462-67-3.mol
• Article Data: 137

Chemical Properties

• Boiling Point: 656.857°C at 760 mmHg
• Flash Point: 247.964°C
• Appearance: /
• Density: 1.187g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE(83462-67-3)
• EPA Substance Registry System: METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE(83462-67-3)

Safety Data

• Hazardous Substances Data: 83462-67-3(Hazardous Substances Data)

Usage

Description

METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE, with the CAS number 83462-67-3, is a complex organic compound that plays a significant role in the field of organic synthesis. It is a derivative of α-D-mannopyranoside, where four hydroxyl groups are protected by benzyl groups at the 2, 3, 4, and 6 positions. METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE is essential for various chemical reactions and processes, particularly in the synthesis of complex carbohydrates and glycoconjugates.

Uses

Used in Organic Synthesis:
METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE is used as a key intermediate in organic synthesis for the preparation of various complex carbohydrates and glycoconjugates. Its benzyl-protected structure allows for selective reactions and manipulations, making it a valuable building block in the synthesis of biologically active compounds and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE is used as a precursor for the synthesis of glycoconjugate drugs. These drugs have potential applications in the treatment of various diseases, including cancer, infectious diseases, and autoimmune disorders. METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE's ability to form complex carbohydrate structures makes it a crucial component in the development of targeted drug delivery systems and vaccines.
Used in Research and Development:
METHYL 2,3,4,6-TETRA-O-BENZYL-Α-D-MANNOPYRANOSIDE is also used in research and development for the study of carbohydrate chemistry, glycobiology, and glycoengineering. Its unique structure allows researchers to investigate the role of carbohydrates in biological processes and develop new methods for the synthesis of complex carbohydrate structures.

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/t31?,32-,33+,34-,35-/m1/s1

Upstream product

• 67-56-1 methanol 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 144490-57-3 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-αβ-D-glucopyranoside 
• 681-84-5 tetramethylorthosilicate 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 
• 100-44-7 benzyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 172847-89-1 2',4',6'-Trimethoxyphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 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 

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 
• 81972-19-2 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene 
• 82659-52-7 1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 78890-68-3 1-deoxy-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 35094-65-6 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 4356-77-8 acetyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 35303-86-7 (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol 

Relevant articles and documents

Streamlined access to carbohydrate building blocks: Methyl 2,4,6-tri-O-benzyl-α-D-glucopyranoside

Presented herein is an improved synthesis of a common 3-OH glycosyl acceptor. This compound is a building block that is routinely synthesized by many research groups to be used in glycosylation refinement studies. The only known direct synthesis by Koto lacks regioselectivity and relies on chromatography separation using hazardous solvents. Our improved synthetic approach relies on Koto's selective benzylation protocol, but it is followed by acylation-purification-deacylation sequence. Although this approach involves additional manipulations, it provides consistent results and is superior to other indirect strategies. Also obtained, albeit in minor quantities, is 4-OH acceptor, another common building block.

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.

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.