O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate
CAS No.:315208-15-2
Molecular Formula:C₄₂H₄₅Cl₃N₂O₁₇
Molecular Weight:956.182
Hs Code.:

O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

Synonyms:O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

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Chemical Property of O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

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Technology Process of O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

There total 10 articles about O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-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: 85.0%

: 545-06-2
trichloroacetonitrile

: 315208-49-2
O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose

: 315208-15-2
O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-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:

: 100-47-0
benzonitrile

: 315208-15-2
O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / triethylamine; propionitrile / 1.5 h / 20 °C

2: 72 percent / TMSOTf; 4A molecular sieves / CH₂Cl₂ / 1 h / 20 °C

3: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / -20 °C

4: 85 percent / DBU / CH₂Cl₂ / 1 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; propiononitrile; In tetrahydrofuran; dichloromethane; 1: Acylation / 2: Condensation / 3: desilylation / 4: Addition;
DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b

Reference yield:

: 303082-31-7
dimethyl(thexyl)silyl 4,6-O-benzylidene-2-deoxy-2-(dimethylmaleimido)-β-D-glucopyranoside

: 315208-15-2
O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-benzoyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / pyridine / 1 h / 20 °C

2: 86 percent / ethanethiol; pTsOH / CH₂Cl₂ / 2 h / 20 °C

3: 87 percent / triethylamine; propionitrile / 1.5 h / 20 °C

4: 72 percent / TMSOTf; 4A molecular sieves / CH₂Cl₂ / 1 h / 20 °C

5: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / -20 °C

6: 85 percent / DBU / CH₂Cl₂ / 1 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; ethanethiol; propiononitrile; In tetrahydrofuran; dichloromethane; 1: Acetylation / 2: Ring cleavage / 3: Acylation / 4: Condensation / 5: desilylation / 6: Addition;
DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b