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-glucopyranose

Base Information

Chemical Name: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-glucopyranose
CAS No.:315208-47-0
Molecular Formula:C₅₃H₅₁NO₁₄
Molecular Weight:925.986
Hs Code.:

Synonyms: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-glucopyranose

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Chemical Property of 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-glucopyranose

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Technology Process of 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-glucopyranose

There total 9 articles about 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-glucopyranose 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: 90.0%

: 315208-46-9
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

: 315208-47-0
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-glucopyranose

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h;
DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b

Reference yield:

: 303082-23-7
thexyldimethylsilyl 2-deoxy-2-(dimethylmaleoylimido)-3,6-di-O-benzyl-β-D-glucopyranoside

: 315208-47-0
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-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / TMSOTf / CH₂Cl₂ / 0.5 h / 20 °C

2: 85 percent / sodium methoxide / methanol / 8 h / 20 °C

3: 82 percent / triethylamine / acetonitrile; CH₂Cl₂ / 2 h / -70 °C

4: 97 percent / pyridine / CH₂Cl₂ / 5 h / -15 °C

5: 85 percent / acetonitrile / 20 °C

6: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h

With pyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium methylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1: Condensation / 2: Deacetylation / 3: Acylation / 4: Acylation / 5: Substitution / 6: desilylation;
DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b

Reference yield:

: 315208-18-5
3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside

: 315208-47-0
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-glucopyranose

Guidance literature:: Multi-step reaction with 9 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

5: 85 percent / sodium methoxide / methanol / 8 h / 20 °C

6: 82 percent / triethylamine / acetonitrile; CH₂Cl₂ / 2 h / -70 °C

7: 97 percent / pyridine / CH₂Cl₂ / 5 h / -15 °C

8: 85 percent / acetonitrile / 20 °C

9: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium methylate; di(n-butyl)tin oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 1: Condensation / 2: Deacetylation / 3: Etherification / 4: Condensation / 5: Deacetylation / 6: Acylation / 7: Acylation / 8: Substitution / 9: desilylation;
DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b