Methyl beta-D-glucopyranoside 2,4,6-triacetate

Base Information

• Chemical Name: Methyl beta-D-glucopyranoside 2,4,6-triacetate
• CAS No.: 92008-11-2
• Molecular Formula: C13H20O9
• Molecular Weight: 0
• Mol file: 92008-11-2.mol

Synonyms:Methyl 2,4,6-tri-O-acetyl-beta-D-glucopyranoside;Methyl beta-D-glucopyranoside 2,4,6-triacetate

Chemical Property of Methyl beta-D-glucopyranoside 2,4,6-triacetate

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl beta-D-glucopyranoside 2,4,6-triacetate

There total 3 articles about Methyl beta-D-glucopyranoside 2,4,6-triacetate 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: 75.2%

2,4,6-Tri-O-acetyl-3-O-trityl-β-methyl-D-glucopyranoside (117991-64-7) + 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl-1-deoxy-1-thiocyanate (127066-72-2) → 2,4,6-Tri-O-acetyl-β-methyl-D-glucopyranoside (92008-11-2) + methyl-2,4,6-tri-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside (139710-66-0)

Guidance literature:

With triphenylmethyl perchlorate; In dichloromethane; at 20 ℃; for 2.5h; Product distribution; var. ratios of substrates, promoters, solvents, temperatures and reaction times;

Reference yield: 70.0%

methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4860-85-9) → methyl 6-O-acetyl-β-D-glucopyranoside (20771-12-4) + Methyl 4,6-di-O-acetyl-β-D-glucopyranoside (20771-17-9) + 2,4,6-Tri-O-acetyl-β-methyl-D-glucopyranoside (92008-11-2) + 4-O-acetyl-methyl β-D-glucopyranoside (51897-71-3)

Guidance literature:

With Neisseria sicca SB cellulose acetate esterase; In phosphate buffer; at 20 ℃; for 0.333333h; pH=7.0; Further Variations:; time; Product distribution;

DOI:10.1271/bbb.69.1292

Reference yield: 53.0%

acetyl chloride (75-36-5) + methyl beta-D-glucopyranoside (709-50-2) → methyl 6-O-acetyl-β-D-glucopyranoside (20771-12-4) + 2,4,6-Tri-O-acetyl-β-methyl-D-glucopyranoside (92008-11-2) + methyl 2,3,6-tri-O-acetyl-β-D-glucopyranoside (31873-37-7)

Guidance literature:

methyl beta-D-glucopyranoside; With di(n-butyl)tin oxide; In methanol; at 70 ℃; for 2h;

acetyl chloride; In toluene; at 0 - 22 ℃; for 6h;

DOI:10.1021/jo0620821

upstream raw materials:

2,4,6-Tri-O-acetyl-3-O-trityl-β-methyl-D-glucopyranoside

3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl-1-deoxy-1-thiocyanate

acetyl chloride

methyl beta-D-glucopyranoside

Downstream raw materials:

2,4,6-Tri-O-acetyl-3-O-trityl-β-methyl-D-glucopyranoside

methyl-2,4,6-tri-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside

methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside

Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester