(2S,4S,5R)-2-<(1R)-(1-hydroxy-1-phenyl)but-3-enyl>-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine

Base Information

• Chemical Name: (2S,4S,5R)-2-<(1R)-(1-hydroxy-1-phenyl)but-3-enyl>-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine
• CAS No.: 156365-91-2
• Molecular Formula: C₂₅H₃₁NO₄
• Molecular Weight: 409.525

Synonyms:(2S,4S,5R)-2-<(1R)-(1-hydroxy-1-phenyl)but-3-enyl>-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine

Chemical Property of (2S,4S,5R)-2-<(1R)-(1-hydroxy-1-phenyl)but-3-enyl>-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine

Chemical Property:

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Technology Process of (2S,4S,5R)-2-<(1R)-(1-hydroxy-1-phenyl)but-3-enyl>-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine

There total 4 articles about (2S,4S,5R)-2-<(1R)-(1-hydroxy-1-phenyl)but-3-enyl>-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine 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: 97.0%

(2S,4S,5R)-4-methyl-2-(1-oxo-1-phenyl)methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine (156365-81-0) + allyl-trimethyl-silane (762-72-1) → (2S,4S,5R)-2-<(1R)-(1-hydroxy-1-phenyl)but-3-enyl>-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine (156365-91-2)

Guidance literature:

With titanium tetrachloride; In dichloromethane; -78 deg C to -20 deg C;

DOI:10.1016/0040-4020(95)00145-X

Reference yield:

phenylglyoxal hydrate (1074-12-0) → (2S,4S,5R)-2-<(1R)-(1-hydroxy-1-phenyl)but-3-enyl>-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine (156365-91-2)

Guidance literature:

Multi-step reaction with 3 steps

1: molecular sieves 4A / CH₂Cl₂ / 0.5 h / Ambient temperature

2: ethyl acetate / 1.5 h / Heating

3: 96 percent / TiCl₄ / CH₂Cl₂ / -78 °C

With 4 A molecular sieve; titanium tetrachloride; In dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)76893-6

Reference yield:

(1R,2S)-norephedrine (492-41-1,58550-13-3,757124-50-8) → (2S,4S,5R)-2-<(1R)-(1-hydroxy-1-phenyl)but-3-enyl>-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine (156365-91-2)

Guidance literature:

Multi-step reaction with 3 steps

1: molecular sieves 4A / CH₂Cl₂ / 0.5 h / Ambient temperature

2: ethyl acetate / 1.5 h / Heating

3: 96 percent / TiCl₄ / CH₂Cl₂ / -78 °C

With 4 A molecular sieve; titanium tetrachloride; In dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)76893-6

upstream raw materials:

(2S,4S,5R)-4-methyl-2-(1-oxo-1-phenyl)methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine

allyl-trimethyl-silane

phenylglyoxal hydrate

(1R,2S)-norephedrine

Downstream raw materials:

(2R)-1,2-dihydroxy-2-phenylpent-4-ene

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