2-(N-(phenylsulfonyl)indol-3-yl)ethyl 3-deoxy-2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

Base Information

Chemical Name:2-(N-(phenylsulfonyl)indol-3-yl)ethyl 3-deoxy-2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside
CAS No.:149831-80-1
Molecular Formula:C₅₂H₅₅NO₇SSi
Molecular Weight:866.163
Hs Code.:

Synonyms:2-(N-(phenylsulfonyl)indol-3-yl)ethyl 3-deoxy-2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

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Chemical Property of 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 3-deoxy-2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

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Technology Process of 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 3-deoxy-2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

There total 9 articles about 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 3-deoxy-2,4-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: 47.0%

: 100-39-0
benzyl bromide

: 149831-79-8
2-(N-(phenylsulfonyl)indol-3-yl)ethyl 3-deoxy-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

: 149831-80-1
2-(N-(phenylsulfonyl)indol-3-yl)ethyl 3-deoxy-2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

Guidance literature:: With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; Petroleum ether;

Reference yield:

: 526-55-6,930395-07-6
2-(3-indole)-ethanol

: 149831-80-1
2-(N-(phenylsulfonyl)indol-3-yl)ethyl 3-deoxy-2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

2: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, 16 h

3: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature

4: 60 percent / 4A molecular sieves, Ag₂O / benzene; hexane / 72 h / Ambient temperature

5: 87 percent / CH₃ONa / methanol / 90 h / Ambient temperature

6: 87 percent / imidazole / dimethylformamide / 24 h / 50 °C

7: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, RT, 1 h, 2.) THF, RT, 3 d

With 1H-imidazole; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; benzene;

Reference yield:

: 115938-44-8
1,2,4,6-tetra-O-acetyl-3-deoxy-β-D-ribo-hexoopyranose

: 149831-80-1
2-(N-(phenylsulfonyl)indol-3-yl)ethyl 3-deoxy-2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: HBr, acetic acid / 0.5 h / Ambient temperature

2: 60 percent / 4A molecular sieves, Ag₂O / benzene; hexane / 72 h / Ambient temperature

3: 87 percent / CH₃ONa / methanol / 90 h / Ambient temperature

4: 87 percent / imidazole / dimethylformamide / 24 h / 50 °C

5: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, RT, 1 h, 2.) THF, RT, 3 d

With 1H-imidazole; 4 A molecular sieve; hydrogen bromide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; silver(l) oxide; In methanol; hexane; N,N-dimethyl-formamide; benzene;