(S)-9-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid

Base Information

Chemical Name:(S)-9-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid
CAS No.:1309597-51-0
Molecular Formula:C₃₉H₄₆N₂O₅Si
Molecular Weight:650.89
Hs Code.:

Synonyms:(S)-9-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid

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Chemical Property of (S)-9-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid

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Technology Process of (S)-9-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid

There total 5 articles about (S)-9-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid 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: 84.0%

: 1309597-57-6
(1S,3S)-9-tert-butyl 3-methyl-2-(but-2-ynyl)-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-3,4-dihydro-1H-pyrido[3,4-b]indole-3,9(2H)-dicarboxylate

: 1309597-51-0
(S)-9-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid

Guidance literature:: With methanol; water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1002/ejoc.201100147

Reference yield:

: 1309597-50-9
(1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole

: 1309597-51-0
(S)-9-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: dmap / acetonitrile / 2 h / 20 °C / Inert atmosphere

2: methanol; water; sodium hydroxide / tetrahydrofuran / 24 h / 20 °C

With methanol; dmap; water; sodium hydroxide; In tetrahydrofuran; acetonitrile;
DOI:10.1002/ejoc.201100147

Reference yield:

: 4299-70-1
L-tryptophan methyl ester

: 1309597-51-0
(S)-9-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: dichloromethane / 40 h / 0 °C / Inert atmosphere; Molecular sieve

1.2: -78 - 20 °C / Inert atmosphere

2.1: potassium carbonate / methanol / 0 - 20 °C / Inert atmosphere

3.1: dmap / acetonitrile / 2 h / 20 °C / Inert atmosphere

4.1: methanol; water; sodium hydroxide / tetrahydrofuran / 24 h / 20 °C

With methanol; dmap; water; potassium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1.1: Pictet-Spengler cyclisation / 1.2: Pictet-Spengler cyclisation;
DOI:10.1002/ejoc.201100147