8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: 8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside
• CAS No.: 81413-15-2
• Molecular Formula: C₃₄H₄₆O₁₀
• Molecular Weight: 614.733
• Mol file: 81413-15-2.mol

Synonyms:8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside

Chemical Property of 8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside

There total 6 articles about 8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside 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: 49.0%

methyl 9-hydroxynonanoate (34957-73-8) + 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranosyl chloride (81413-14-1) → 8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-β-D-glucopyranoside (81413-16-3) + 8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside (81413-15-2)

Guidance literature:

With mercury(II) cyanide; mercury dibromide; In dichloromethane; -70 deg C, then allowed warm to room temperature;

DOI:10.1139/v82-045

Reference yield:

methyl 9-hydroxynonanoate (34957-73-8) + 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide (86861-46-3) → 8-methoxycarbonyloctyl 3,6-di-O-benzyl-D-mannopyranoside (81413-15-2,81413-16-3,108167-19-7,134040-44-1)

Guidance literature:

With silver zeolite; In dichloromethane; -78 deg C, 2 h, then RT, 16 h;

DOI:10.1016/0008-6215(91)80118-7

Reference yield:

benzyl bromide (100-39-0) → 8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside (81413-15-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / barium oxide / dimethylformamide / 3 h / 60 °C

2: 79 percent / conc. sulfuric acid / 0.5 h

3: 100 percent / dichloromethyl methyl ether, zinc chloride / CH₂Cl₂ / 1.5 h

4: 49 percent / mercuric cyanide, mercuric bromide / CH₂Cl₂ / -70 deg C, then allowed warm to room temperature

With Dichloromethyl methyl ether; sulfuric acid; mercury(II) cyanide; mercury dibromide; zinc(II) chloride; barium(II) oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1139/v82-045

upstream raw materials:

methyl 9-hydroxynonanoate

3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide

3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranosyl chloride

benzyl bromide

Downstream raw materials:

8-methoxycarbonyloctyl 2,4-di-O-benzyl-α-D-glucopyranoside

8-methoxycarbonyloctyl-2,4-di-O-benzyl-3,6-di-O-<2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl>-α-D-glucopyranoside

8-methoxycarbonyloctyl 2,4-di-O-benzyl-β-D-mannopyranoside

8-methoxycarbonyloctyl 2,4-di-O-benzyl-3,6-di-O-p-nitrobenzoyl-α-D-mannopyranoside