METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-ALPHA-D-MANNOPYRANOSIDE

Base Information

• Chemical Name: METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-ALPHA-D-MANNOPYRANOSIDE
• CAS No.: 64550-71-6
• Molecular Formula: C15H22 O9 S
• Molecular Weight: 378.4
• Hs Code.: 29389090
• Mol file: 64550-71-6.mol

Synonyms:a-D-Mannopyranoside, methyl1-thio-, tetraacetate (9CI)

Chemical Property of METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-ALPHA-D-MANNOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 5.86E-08mmHg at 25°C
• Melting Point: 123.0 to 127.0 °C
• Refractive Index: 1.502
• Boiling Point: 440.5oC at 760 mmHg
• Flash Point: 206.9oC
• Density: 1.29g/cm3
• Storage Temp.: −20°C
• Solubility.: slightly sol. in Chloroform

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 2,3,4,6-tetra-O-acetyl-a-D-thiomannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-ALPHA-D-MANNOPYRANOSIDE

There total 13 articles about METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-ALPHA-D-MANNOPYRANOSIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

acetic anhydride (108-24-7) + methyl 1-thio-α-D-mannopyranoside (80734-76-5) → methyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (64550-71-6)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; at 20 ℃; for 0.583333h; Neat (no solvent);

DOI:10.1016/j.tetlet.2011.08.141

Reference yield: 86.0%

2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide (57030-42-9) + methyl iodide (74-88-4) → methyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (64550-71-6)

Guidance literature:

With triethylamine; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2016.04.015

Reference yield: 77.0%

D-Mannose (530-26-7) + acetic anhydride (108-24-7) + methyl iodide (74-88-4) → methyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (64550-71-6)

Guidance literature:

Multistep reaction.;

DOI:10.1021/jo070670o

upstream raw materials:

acetic anhydride

methyl 1-thio-α-D-mannopyranoside

D-Mannose pentaacetate

Trimethyl(methylthio)silane

Downstream raw materials:

benzyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->2)-O-(4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

benzyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-(4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

methyl 2-O(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside

methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside

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