allyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: allyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 78139-21-6
• Molecular Formula: C₄₇H₅₆N₂O₁₁
• Molecular Weight: 824.968

Synonyms:allyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 8 articles about allyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-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: 62.0%

allyl O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (126628-26-0) → allyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (78139-21-6)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)85021-9

Reference yield:

chitobiose octaacetate (7284-18-6) → allyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (78139-21-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) trimethylsilyl trifluoromethanesulfonate, 2.) triethylamine / 1.) 1,2-dichloroethane, 50 deg C, 5 h

2: 53 percent / trifluoromethanesulfonic acid / CHCl₃ / 5 h / 90 °C

3: 97 percent / sodium methoxide / methanol / 3 h / Ambient temperature

4: 1.) p-toluenesulfonic acid monohydrate, 2.) barium oxide, barium hydroxyde octahydrate / 1.) DMF, ca. 1.33 kPa, 60-80 deg C, 2 h, 2.) DMF, 16 h, room temperature

5: 62 percent / hydrogen chloride, sodium cyanoborohydride, 3A molecular sieves / dimethylformamide; diethyl ether; tetrahydrofuran

With hydrogenchloride; barium dihydroxide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; barium(II) oxide; trifluorormethanesulfonic acid; In tetrahydrofuran; methanol; diethyl ether; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)85021-9

Reference yield:

(3aR)-7c-acetoxy-5c-acetoxymethyl-2-methyl-(3ar,7ac)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-6t-yl tri-O-acetyl-2-acetylamino-β-D-2-deoxy-glucopyranoside (22854-03-1) → allyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (78139-21-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 53 percent / trifluoromethanesulfonic acid / CHCl₃ / 5 h / 90 °C

2: 97 percent / sodium methoxide / methanol / 3 h / Ambient temperature

3: 1.) p-toluenesulfonic acid monohydrate, 2.) barium oxide, barium hydroxyde octahydrate / 1.) DMF, ca. 1.33 kPa, 60-80 deg C, 2 h, 2.) DMF, 16 h, room temperature

4: 62 percent / hydrogen chloride, sodium cyanoborohydride, 3A molecular sieves / dimethylformamide; diethyl ether; tetrahydrofuran

With hydrogenchloride; barium dihydroxide; 3 A molecular sieve; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; barium(II) oxide; trifluorormethanesulfonic acid; In tetrahydrofuran; methanol; diethyl ether; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)85021-9

upstream raw materials:

allyl 2-acetamido-4-O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

allyl O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

allyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-SD-glucopyranoside

allyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside

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