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

Base Information

• Chemical Name: benzyl O-(2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-α-D-glucopyranosyl-(1->2)-3,4,6,-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 112289-04-0
• Molecular Formula: C₄₉H₆₀O₁₆
• Molecular Weight: 905.006

Synonyms:benzyl O-(2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-α-D-glucopyranosyl-(1->2)-3,4,6,-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of benzyl O-(2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-α-D-glucopyranosyl-(1->2)-3,4,6,-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of benzyl O-(2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-α-D-glucopyranosyl-(1->2)-3,4,6,-tri-O-benzyl-β-D-glucopyranoside

There total 13 articles about benzyl O-(2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-α-D-glucopyranosyl-(1->2)-3,4,6,-tri-O-benzyl-β-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: 93.0%

benzyl-O-(3,4,6-tri-O-acetyl-2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->2)-3,4-6-tri-O-benzyl-β-D-glucopyranoside (112289-05-1) → benzyl O-(2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-α-D-glucopyranosyl-(1->2)-3,4,6,-tri-O-benzyl-β-D-glucopyranoside (112289-04-0)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(87)80204-5

Reference yield:

methyl 2-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside (20770-92-7) → benzyl O-(2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-α-D-glucopyranosyl-(1->2)-3,4,6,-tri-O-benzyl-β-D-glucopyranoside (112289-04-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / acetic acid / 0.25 h / 100 °C

2: 81 percent / M sulfuric acid / 16 h / 100 °C

3: pyridine

4: 94 percent / hydrogen bromide in acetic acid / CH₂Cl₂ / 0.5 h / 0 °C

5: 88 percent / tetraethylammonium chloride / acetonitrile / Ambient temperature

6: 71 percent / silver perchlorate, molecular sieve / diethyl ether; 1,2-dimethoxy-ethane / 1 h / Ambient temperature

7: 92 percent / hydrogen bromide in acetic acid / CH₂Cl₂ / 1.5 h / 0 °C

8: 86 percent / tetraethylammonium chloride / acetonitrile / 0.33 h / Ambient temperature

9: 68 percent / silver perchlorate, molecular sieve / diethyl ether / 3 h / Ambient temperature

10: 93 percent / sodium methoxide / methanol; CH₂Cl₂ / Ambient temperature

With pyridine; molecular sieve; sulfuric acid; tetraethylammonium chloride; hydrogen bromide; sodium methylate; silver perchlorate; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetic acid; acetonitrile;

DOI:10.1016/0008-6215(87)80204-5

Reference yield:

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide (55659-53-5,77790-47-7,93381-69-2,53270-13-6) → benzyl O-(2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-α-D-glucopyranosyl-(1->2)-3,4,6,-tri-O-benzyl-β-D-glucopyranoside (112289-04-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) silver carbonate, Drierite 2) sodium methoxide / 1.) ether:benzene (1:1), room temp., overnight 2) methanol, room temp., 6 h

2: 68 percent / silver perchlorate, molecular sieve / diethyl ether / 3 h / Ambient temperature

3: 93 percent / sodium methoxide / methanol; CH₂Cl₂ / Ambient temperature

With calcium sulfate; molecular sieve; sodium methylate; silver perchlorate; silver carbonate; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/0008-6215(87)80204-5

upstream raw materials:

benzyl-O-(3,4,6-tri-O-acetyl-2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->2)-3,4-6-tri-O-benzyl-β-D-glucopyranoside

methyl 2-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside

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

benzyl 3,4,6-tetra-O-benzyl-β-G-glucopyranoside

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