2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside
CAS No.:174149-09-8
Molecular Formula:C₄₁H₅₄O₆Si₂
Molecular Weight:699.047
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

There total 5 articles about 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-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: 70.0%

: 152771-01-2
2-(Trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranoside

: 58479-61-1
tert-butylchlorodiphenylsilane

: 174149-09-8
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

Guidance literature:: With pyridine; at 20 ℃; for 12h;
DOI:10.1080/07328300500495878

Reference yield:

: 81342-44-1
(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 174149-09-8
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: Amberlite IRA 910 / methanol / 2 h / 25 °C

2: 89 percent / PTSA / acetonitrile / 3 h / 25 °C

3: 1.) NaH / 1.) DMF, 20 deg C, 2 h, 2.) 25 deg C, 3 h

4: 0.5 M HCl / methanol / 2 h / Heating

5: imidazole / dimethylformamide / 5 h / 25 °C

With 1H-imidazole; hydrogenchloride; Amberlite IRA 910; sodium hydride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo951067l

Reference yield:

: 81336-89-2,81336-96-1,117252-95-6,132871-94-4,117252-72-9
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triol

: 174149-09-8
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / PTSA / acetonitrile / 3 h / 25 °C

2: 1.) NaH / 1.) DMF, 20 deg C, 2 h, 2.) 25 deg C, 3 h

3: 0.5 M HCl / methanol / 2 h / Heating

4: imidazole / dimethylformamide / 5 h / 25 °C

With 1H-imidazole; hydrogenchloride; sodium hydride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo951067l