(S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)propanoate

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Chemical Name:(S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)propanoate
CAS No.:1422538-31-5
Molecular Formula:C₃₄H₄₇N₃O₅Si
Molecular Weight:605.85
Hs Code.:

Synonyms:(S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)propanoate

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Chemical Property of (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)propanoate

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Technology Process of (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)propanoate

There total 9 articles about (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)propanoate 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: 70.0%

: 1422538-30-4
(2R,4S)-benzyl 2-tert-butyl-5-oxo-4-(2-oxoethyl)-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate

: 2491-20-5
L-alanine methyl ester hydrochloride

: 1422538-31-5
(S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)propanoate

Guidance literature:: (2R,4S)-benzyl 2-tert-butyl-5-oxo-4-(2-oxoethyl)-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate; L-alanine methyl ester hydrochloride; With sodium acetate; In methanol; for 1h; Molecular sieve; Inert atmosphere;

With sodium cyanoborohydride; In methanol; at 20 ℃; Inert atmosphere;

With benzotriazol-1-ol; In toluene; for 6h; Reflux; Inert atmosphere;
DOI:10.1021/jo302737j

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 1422538-31-5
(S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)propanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: stannic tetrachloride pentahydrate / ethyl acetate / 48 h / 0 - 20 °C / Inert atmosphere

3.1: lithium hydroxide / tetrahydrofuran; water / 4 h / 20 °C / Inert atmosphere

4.1: sodium hydroxide / water; ethanol / 1 h / 20 °C / Inert atmosphere

4.2: 12 h / Inert atmosphere; Molecular sieve; Reflux

5.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 °C / Inert atmosphere

5.2: -78 - -30 °C / Inert atmosphere

6.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 20 h / Inert atmosphere

7.1: sodium periodate / water / 24 h / 20 °C / Inert atmosphere

8.1: sodium acetate / methanol / 1 h / Molecular sieve; Inert atmosphere

8.2: 20 °C / Inert atmosphere

8.3: 6 h / Reflux; Inert atmosphere

With sodium periodate; osmium(VIII) oxide; stannic tetrachloride pentahydrate; sodium acetate; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; acetone; toluene;
DOI:10.1021/jo302737j

Reference yield:

: 151872-21-8
(R)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid methyl ester

: 1422538-31-5
(S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)propanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: stannic tetrachloride pentahydrate / ethyl acetate / 48 h / 0 - 20 °C / Inert atmosphere

3.1: lithium hydroxide / tetrahydrofuran; water / 4 h / 20 °C / Inert atmosphere

4.1: sodium hydroxide / water; ethanol / 1 h / 20 °C / Inert atmosphere

4.2: 12 h / Inert atmosphere; Molecular sieve; Reflux

5.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 °C / Inert atmosphere

5.2: -78 - -30 °C / Inert atmosphere

6.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 20 h / Inert atmosphere

7.1: sodium periodate / water / 24 h / 20 °C / Inert atmosphere

8.1: sodium acetate / methanol / 1 h / Molecular sieve; Inert atmosphere

8.2: 20 °C / Inert atmosphere

8.3: 6 h / Reflux; Inert atmosphere

With sodium periodate; osmium(VIII) oxide; stannic tetrachloride pentahydrate; sodium acetate; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; acetone; toluene;
DOI:10.1021/jo302737j