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

Base Information

• Chemical Name: (2R,4R)-benzyl 4-allyl-2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate
• CAS No.: 1422538-29-1
• Molecular Formula: C₃₆H₅₀N₂O₄Si
• Molecular Weight: 602.889

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

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

Chemical Property:

Purity/Quality:

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

There total 6 articles about (2R,4R)-benzyl 4-allyl-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: 82.0%

(2R,4R)-benzyl 2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate (1422538-28-0) + allyl bromide (106-95-6) → (2R,4R)-benzyl 4-allyl-2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate (1422538-29-1)

Guidance literature:

(2R,4R)-benzyl 2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1h; Inert atmosphere;

allyl bromide; In tetrahydrofuran; toluene; at -78 - -30 ℃; Inert atmosphere;

DOI:10.1021/jo302737j

Reference yield:

(R)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid methyl ester (151872-21-8) → (2R,4R)-benzyl 4-allyl-2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate (1422538-29-1)

Guidance literature:

Multi-step reaction with 5 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

With stannic tetrachloride pentahydrate; potassium hexamethylsilazane; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; ethanol; water; ethyl acetate; toluene;

DOI:10.1021/jo302737j

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (2R,4R)-benzyl 4-allyl-2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate (1422538-29-1)

Guidance literature:

Multi-step reaction with 5 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

With stannic tetrachloride pentahydrate; potassium hexamethylsilazane; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; ethanol; water; ethyl acetate; toluene;

DOI:10.1021/jo302737j

upstream raw materials:

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

triisopropylsilyl chloride

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

allyl bromide

Downstream raw materials:

(S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate

C₃₇H₄₈N₆O₆

C₄₆H₅₇N₇O₇

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

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