tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside
CAS No.:340290-26-8
Molecular Formula:C₄₀H₄₉NO₉Si
Molecular Weight:715.916
Hs Code.:

Synonyms:tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside

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

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

There total 1 articles about tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-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: 88.0%

: 701-99-5
Phenoxyacetyl chloride

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

: 340290-26-8
tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside

Guidance literature:: With pyridine; for 2h;
DOI:10.1016/S0008-6215(01)00024-6

Reference yield: 79.0%

: 340290-26-8
tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside

: Phenoxy-acetic acid (2R,3S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-hydroxy-tetrahydro-pyran-3-yl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;
DOI:10.1016/S0008-6215(01)00024-6

Reference yield:

: 340290-26-8
tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside

: 340290-42-8
benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 79 percent / TBAF; AcOH / tetrahydrofuran

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

3: 71 percent / TMSOTf / acetonitrile / 20 °C

4: 86 percent / AcOH; TBAF / tetrahydrofuran

5: 82 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

6: 82 percent / TMSOTf / acetonitrile / 2 h / 20 °C

7: 82 percent / NaOMe / methanol; tetrahydrofuran

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