tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
CAS No.:340290-29-1
Molecular Formula:C₆₆H₇₆N₂O₁₅Si
Molecular Weight:1165.42
Hs Code.:

tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Synonyms:tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

There total 5 articles about tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-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: 71.0%

: 216877-47-3
tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside

: 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-D-glucopyranoside trichloroacetimidiate

: 340290-29-1
tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃;
DOI:10.1016/S0008-6215(01)00024-6

Reference yield:

: 701-99-5
Phenoxyacetyl chloride

: 340290-29-1
tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / pyridine / 2 h

2: 79 percent / TBAF; AcOH / tetrahydrofuran

3: 86 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

4: 71 percent / TMSOTf / acetonitrile / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/S0008-6215(01)00024-6

Reference yield:

: 216877-47-3
tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside

: 340290-29-1
tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / pyridine / 2 h

2: 79 percent / TBAF; AcOH / tetrahydrofuran

3: 86 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

4: 71 percent / TMSOTf / acetonitrile / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/S0008-6215(01)00024-6