dimethyl(thexyl)silyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Base Information

• Chemical Name: dimethyl(thexyl)silyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
• CAS No.: 315208-42-5
• Molecular Formula: C₅₁H₆₅NO₁₄Si
• Molecular Weight: 944.161

Synonyms:dimethyl(thexyl)silyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Chemical Property of dimethyl(thexyl)silyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of dimethyl(thexyl)silyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

There total 5 articles about dimethyl(thexyl)silyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-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: 85.0%

Acetic acid (2R,4aR,6S,7R,8S,8aR)-7-acetoxy-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (315208-41-4) + thexyldimethylsilyl 2-deoxy-2-(dimethylmaleoylimido)-3,6-di-O-benzyl-β-D-glucopyranoside (303082-23-7) → dimethyl(thexyl)silyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (315208-42-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b

Reference yield:

chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → dimethyl(thexyl)silyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (315208-42-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

2: 98 percent / sodium methoxide / methanol / 4 h / 20 °C

3: 85 percent / dibutyltin oxide / toluene / 3 h / Heating

4: 85 percent / TMSOTf / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; sodium methylate; di(n-butyl)tin oxide; In methanol; dichloromethane; toluene; 1: Condensation / 2: Deacetylation / 3: Etherification / 4: Condensation;

DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside (315208-18-5) → dimethyl(thexyl)silyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (315208-42-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

2: 98 percent / sodium methoxide / methanol / 4 h / 20 °C

3: 85 percent / dibutyltin oxide / toluene / 3 h / Heating

4: 85 percent / TMSOTf / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; sodium methylate; di(n-butyl)tin oxide; In methanol; dichloromethane; toluene; 1: Condensation / 2: Deacetylation / 3: Etherification / 4: Condensation;

DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b

upstream raw materials:

Acetic acid (2R,4aR,6S,7R,8S,8aR)-7-acetoxy-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

thexyldimethylsilyl 2-deoxy-2-(dimethylmaleoylimido)-3,6-di-O-benzyl-β-D-glucopyranoside

chlorodimethyl(1,1,2-trimethylpropyl)silane

3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside

Downstream raw materials:

dimethyl(thexyl)silyl O-(3-O-benzoyl-4,6-O-benzylidene-2-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

dimethyl(thexyl)silyl O-(2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

O-(2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

dimethyl(thexyl)silyl O-(3-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

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