benzyl 4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: benzyl 4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside
• CAS No.: 114284-10-5
• Molecular Formula: C₂₃H₃₆O₁₀
• Molecular Weight: 472.533
• Mol file: 114284-10-5.mol

Synonyms:benzyl 4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside

Chemical Property of benzyl 4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside

There total 7 articles about benzyl 4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside 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: 85.0%

benzyl 4-O-(2,4-di-O-acetyl-3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside (114284-09-2) → benzyl 4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside (114284-10-5)

Guidance literature:

With sodium methylate; In methanol; for 24h;

DOI:10.1016/0008-6215(87)80099-X

Reference yield:

benzyl 4-O-allyl-2,3-di-O-methyl-α-L-rhamnopyranoside (114284-04-7) → benzyl 4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside (114284-10-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / 5percent Pd-C / ethanol; acetic acid; H₂O / 72 h / 80 - 90 °C

2: 1) HBr, AcOH; 2) Hg(CN)2 / 1) CH₂Cl₂, 0 deg C, 30 min; 2) CH₂Cl₂, MeCN, several hours

3: 85 percent / sodium methoxide / methanol / 24 h

With hydrogen bromide; sodium methylate; mercury(II) cyanide; acetic acid; palladium on activated charcoal; In methanol; ethanol; water; acetic acid;

DOI:10.1016/0008-6215(87)80099-X

Reference yield:

1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose (43138-65-4) → benzyl 4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside (114284-10-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) boron trifluoride etherate; 2.) triethylamine / 1.) CH₂Cl₂-ether, -5 deg C; 2.) acetone, 24 h

2: 90 percent / HCl / dioxane / 1 h / Heating

3: pyridine

4: 1) HBr, AcOH; 2) Hg(CN)2 / 1) CH₂Cl₂, 0 deg C, 30 min; 2) CH₂Cl₂, MeCN, several hours

5: 85 percent / sodium methoxide / methanol / 24 h

With pyridine; hydrogenchloride; boron trifluoride diethyl etherate; hydrogen bromide; sodium methylate; mercury(II) cyanide; acetic acid; triethylamine; In 1,4-dioxane; methanol;

DOI:10.1016/0008-6215(87)80099-X

upstream raw materials:

benzyl 4-O-(2,4-di-O-acetyl-3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside

O³,O⁶-dimethyl-D-glucose

benzyl 2,3-di-O-methyl-α-L-rhamnopyranoside

benzyl 4-O-allyl-2,3-di-O-methyl-α-L-rhamnopyranoside