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

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-glucopyranosyl trichloroacetimidate
CAS No.:315208-13-0
Molecular Formula:C₅₅H₅₁Cl₃N₂O₁₄
Molecular Weight:1070.37
Hs Code.:

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

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-glucopyranosyl trichloroacetimidate

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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-glucopyranosyl trichloroacetimidate

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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-glucopyranosyl trichloroacetimidate

There total 10 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-glucopyranosyl trichloroacetimidate 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: 95.0%

: 545-06-2
trichloroacetonitrile

: 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

: 315208-13-0
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-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h;
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

: 315208-13-0
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-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 7 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

7: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1: Condensation / 2: Deacetylation / 3: Acylation / 4: Acylation / 5: Substitution / 6: desilylation / 7: Addition;
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

: 315208-13-0
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-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 10 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

10: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium methylate; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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 / 10: Addition;
DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b