2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-vinyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-vinyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
CAS No.:174149-11-2
Molecular Formula:C₄₃H₅₆O₆Si₂
Molecular Weight:725.085
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-vinyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-vinyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-vinyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

There total 7 articles about 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-vinyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 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: 72.0%

: 1826-67-1
vinyl magnesium bromide

: 174149-10-1
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-xylo-hexoglucopyranosid-4-ulose

: 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-vinyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

: 174149-11-2
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-vinyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1021/jo951067l

Reference yield:

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

: 174149-11-2
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-vinyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 7 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

6: DMSO/Ac₂O / 2 h / 65 °C

7: 72 percent / tetrahydrofuran / 2 h / -78 °C

With 1H-imidazole; hydrogenchloride; Amberlite IRA 910; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; 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

: 174149-11-2
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-C-vinyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 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

5: DMSO/Ac₂O / 2 h / 65 °C

6: 72 percent / tetrahydrofuran / 2 h / -78 °C

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