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

Base Information

Chemical Name:(2R,4R)-benzyl 2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate
CAS No.:1422538-28-0
Molecular Formula:C₃₃H₄₆N₂O₄Si
Molecular Weight:562.825
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,4R)-benzyl 2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2R,4R)-benzyl 2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate

There total 5 articles about (2R,4R)-benzyl 2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate 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: 77.0%

: 4480-47-1
t-butylglyoxal

: 1422538-27-9
(R)-2-amino-3-(1-(triisopropylsilyl)-1H-indol-3-yl)propanoic acid

: 501-53-1,94274-21-2
benzyl chloroformate

: 1422538-28-0
(2R,4R)-benzyl 2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate

Guidance literature:: (R)-2-amino-3-(1-(triisopropylsilyl)-1H-indol-3-yl)propanoic acid; With sodium hydroxide; In ethanol; water; at 20 ℃; for 1h; Inert atmosphere;

t-butylglyoxal; In dichloromethane; for 12h; Inert atmosphere; Molecular sieve; Reflux;

benzyl chloroformate; Further stages;
DOI:10.1021/jo302737j

Reference yield:

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

: 1422538-28-0
(2R,4R)-benzyl 2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 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

With stannic tetrachloride pentahydrate; potassium hexamethylsilazane; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; ethanol; water; ethyl acetate;
DOI:10.1021/jo302737j

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 1422538-28-0
(2R,4R)-benzyl 2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 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

With stannic tetrachloride pentahydrate; potassium hexamethylsilazane; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; ethanol; water; ethyl acetate;
DOI:10.1021/jo302737j