2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-4-C-methyl-6-O-triphenylmethyl-β-D-glucopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-4-C-methyl-6-O-triphenylmethyl-β-D-glucopyranoside
CAS No.:172297-70-0
Molecular Formula:C₄₃H₆₈O₆Si₃
Molecular Weight:765.266
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-4-C-methyl-6-O-triphenylmethyl-β-D-glucopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-4-C-methyl-6-O-triphenylmethyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of 2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-4-C-methyl-6-O-triphenylmethyl-β-D-glucopyranoside

There total 7 articles about 2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-4-C-methyl-6-O-triphenylmethyl-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: 76.0%

: 676-58-4
methylmagnesium chloride

: 172297-69-7
2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-6-O-triphenylmethyl-β-D-xylo-hexopyranoside-4-ulose

: 2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-4-C-methyl-6-O-triphenylmethyl-β-D-galactopyranoside

: 172297-70-0
2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-4-C-methyl-6-O-triphenylmethyl-β-D-glucopyranoside

Guidance literature:: In tetrahydrofuran; toluene; at -78 - 25 ℃; for 12h;
DOI:10.1016/0040-4020(95)00693-3

Reference yield:

: 117252-95-6
2-(trimethylsilyl)ethyl β-D-galactopyranoside

: 172297-70-0
2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-4-C-methyl-6-O-triphenylmethyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / p-TsOH / acetonitrile / Ambient temperature

2: 99 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 96 percent / H₂ / 10percent Pd-C / acetic acid / 24 h / 760 Torr / Ambient temperature

4: 89 percent / DMAP, Et₃N / dimethylformamide / 120 h / Ambient temperature

5: 84 percent / pyridinium dichromate, Ac₂O / CH₂Cl₂ / 3 h / 40 °C

6: 76 percent / tetrahydrofuran; toluene / 12 h / -78 - 25 °C

With 1H-imidazole; dmap; dipyridinium dichromate; hydrogen; acetic anhydride; triethylamine; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/0040-4020(95)00693-3

Reference yield:

: 117252-96-7
2-(trimethylsilyl)ethyl 4,6-di-O-benzylidene-β-D-galactopyranoside

: 172297-70-0
2-(trimethylsilyl)ethyl 2,3-di-O-tertbutyldimethylsilyl-4-C-methyl-6-O-triphenylmethyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 96 percent / H₂ / 10percent Pd-C / acetic acid / 24 h / 760 Torr / Ambient temperature

3: 89 percent / DMAP, Et₃N / dimethylformamide / 120 h / Ambient temperature

4: 84 percent / pyridinium dichromate, Ac₂O / CH₂Cl₂ / 3 h / 40 °C

5: 76 percent / tetrahydrofuran; toluene / 12 h / -78 - 25 °C

With 1H-imidazole; dmap; dipyridinium dichromate; hydrogen; acetic anhydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0040-4020(95)00693-3