ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate

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Chemical Name:ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate
CAS No.:862297-63-0
Molecular Formula:C₄₁H₄₆N₄O₅SSi
Molecular Weight:734.992
Hs Code.:

Synonyms:ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate

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Chemical Property of ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate

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Technology Process of ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate

There total 11 articles about ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate 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: 66.0%

: 862297-62-9
ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate

: 862297-63-0
ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate

Guidance literature:: ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h; Inert atmosphere;

With 2,4,6-Triisopropylbenzenesulfonyl azide; In tetrahydrofuran; toluene; at -78 ℃; for 0.0833333h; Inert atmosphere;

With acetic acid; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.tet.2011.08.094

Reference yield:

: 1074-85-7
(1H-indol-4-yl)methanol

: 862297-63-0
ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 95 percent / imidazole / tetrahydrofuran / 16 h / 20 °C

2.1: 82 percent / POCl₃ / pyridine / 0.75 h / 35 °C

3.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

4.1: LiCl; DBN / acetonitrile / 0.25 h / 20 °C

4.2: 62 percent / acetonitrile / 2 h / 20 °C

5.1: PhSCu / tetrahydrofuran / 1 h / -40 - 0 °C

5.2: 53 percent / tetrahydrofuran / -40 - 20 °C

6.1: 62 percent / KHMDS; trisyl azide; AcOH / tetrahydrofuran / -78 °C

With 1H-imidazole; dmap; 2,6-dichloro-benzonitrile; 2,4,6-Triisopropylbenzenesulfonyl azide; copper(I) thiophenolate; potassium hexamethylsilazane; acetic acid; triethylamine; lithium chloride; trichlorophosphate; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile; 4.2: Horner-Wadsworth-Emmons reaction / 5.2: Michael addition;
DOI:10.1039/b417625c

Reference yield:

: 862297-60-7
4-[(tert-butyldiphenylsilyloxy)methyl]indole

: 862297-63-0
ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 82 percent / POCl₃ / pyridine / 0.75 h / 35 °C

2.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

3.1: LiCl; DBN / acetonitrile / 0.25 h / 20 °C

3.2: 62 percent / acetonitrile / 2 h / 20 °C

4.1: PhSCu / tetrahydrofuran / 1 h / -40 - 0 °C

4.2: 53 percent / tetrahydrofuran / -40 - 20 °C

5.1: 62 percent / KHMDS; trisyl azide; AcOH / tetrahydrofuran / -78 °C

With dmap; 2,6-dichloro-benzonitrile; 2,4,6-Triisopropylbenzenesulfonyl azide; copper(I) thiophenolate; potassium hexamethylsilazane; acetic acid; triethylamine; lithium chloride; trichlorophosphate; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile; 3.2: Horner-Wadsworth-Emmons reaction / 4.2: Michael addition;
DOI:10.1039/b417625c