benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-β-D-galactopyranoside

Base Information

• Chemical Name: benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-β-D-galactopyranoside
• CAS No.: 93661-21-3
• Molecular Formula: C₄₉H₅₆O₁₄
• Molecular Weight: 868.975
• Mol file: 93661-21-3.mol

Synonyms:benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-β-D-galactopyranoside

Chemical Property of benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-β-D-galactopyranoside

There total 6 articles about benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-β-D-galactopyranoside 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: 87.0%

Benzyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside (57783-81-0) + 2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucopyranosyl bromide (93173-32-1) → benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-β-D-galactopyranoside (93661-21-3)

Guidance literature:

With mercury(II) cyanide; In nitromethane; benzene; at 45 ℃; for 16h;

DOI:10.1016/0008-6215(84)85204-0

Reference yield:

benzyl 2,3-di-O-benzyl-4,6-ol-β-D-galactopyranoside (74801-06-2) → benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-β-D-galactopyranoside (93661-21-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / tetrabutylammonium hydrogensulfate, 5 percent sodium hydroxide / CH₂Cl₂ / 10 h / Heating

2: 87 percent / mercuric cyanide / benzene; nitromethane / 16 h / 45 °C

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; mercury(II) cyanide; In nitromethane; dichloromethane; benzene;

DOI:10.1016/0008-6215(84)85204-0

Reference yield:

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (20316-77-2) → benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-β-D-galactopyranoside (93661-21-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / Amberlite IR-120(H+) resin / H₂O / 7 h / 60 °C

2: 84 percent / sodium acetate / 0.42 h / Heating

3: 88 percent / hydrogen bromide / CH₂Cl₂; acetic acid / 0.5 h / 0 °C

4: 87 percent / mercuric cyanide / benzene; nitromethane / 16 h / 45 °C

With Amberlite IR-120(H+) resin; hydrogen bromide; sodium acetate; mercury(II) cyanide; In nitromethane; dichloromethane; water; acetic acid; benzene;

DOI:10.1016/0008-6215(84)85204-0

upstream raw materials:

Benzyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside

2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucopyranosyl bromide

benzyl 2,3-di-O-benzyl-4,6-ol-β-D-galactopyranoside

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

Downstream raw materials:

benzyl 4-O-(2-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

benzyl 4-O-(3-O-allyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

benzyl 4-O-(3-O-allyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

benzyl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside