(S)-2-((1R,2R)-1-tert-Butyl-1-thioxo-1λ⁵-phospholan-2-yl)-4-phenyl-4,5-dihydro-oxazole

Base Information

• Chemical Name: (S)-2-((1R,2R)-1-tert-Butyl-1-thioxo-1λ⁵-phospholan-2-yl)-4-phenyl-4,5-dihydro-oxazole
• CAS No.: 528813-90-3
• Molecular Formula: C₁₇H₂₄NOPS
• Molecular Weight: 321.423

Synonyms:(S)-2-((1R,2R)-1-tert-Butyl-1-thioxo-1λ⁵-phospholan-2-yl)-4-phenyl-4,5-dihydro-oxazole

Chemical Property of (S)-2-((1R,2R)-1-tert-Butyl-1-thioxo-1λ⁵-phospholan-2-yl)-4-phenyl-4,5-dihydro-oxazole

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Technology Process of (S)-2-((1R,2R)-1-tert-Butyl-1-thioxo-1λ⁵-phospholan-2-yl)-4-phenyl-4,5-dihydro-oxazole

There total 2 articles about (S)-2-((1R,2R)-1-tert-Butyl-1-thioxo-1λ⁵-phospholan-2-yl)-4-phenyl-4,5-dihydro-oxazole 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:

(2S)-2-phenylglycinol (20989-17-7) + (1R,2R)-1-tert-Butyl-1-thioxo-1λ5-phospholane-2-carboxylic acid (528813-80-1) → (S)-2-((1R,2R)-1-tert-Butyl-1-thioxo-1λ5-phospholan-2-yl)-4-phenyl-4,5-dihydro-oxazole (528813-90-3)

Guidance literature:

(2S)-2-phenylglycinol; (1R,2R)-1-tert-Butyl-1-thioxo-1λ⁵-phospholane-2-carboxylic acid; With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 70 ℃;

With methanesulfonyl chloride; In dichloromethane;

DOI:10.1002/anie.200390251

Reference yield:

1-tert-butyl-phospholane 1-sulfide (470480-33-2) → (S)-2-((1R,2R)-1-tert-Butyl-1-thioxo-1λ5-phospholan-2-yl)-4-phenyl-4,5-dihydro-oxazole (528813-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 40 percent / nBuLi; (-)-sparteine / -78 °C

2.1: EDC; HOBT / dimethylformamide / 70 °C

2.2: MsCl / CH₂Cl₂

With n-butyllithium; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; (-)-sparteine; In N,N-dimethyl-formamide;

DOI:10.1002/anie.200390251

Reference yield:

(S)-2-((1R,2R)-1-tert-Butyl-1-thioxo-1λ5-phospholan-2-yl)-4-phenyl-4,5-dihydro-oxazole (528813-90-3) → (S)-2-((1S,2R)-1-tert-Butyl-phospholan-2-yl)-4-phenyl-4,5-dihydro-oxazole

Guidance literature:

With Raney Ni(II); In acetonitrile;

DOI:10.1002/anie.200390251

upstream raw materials:

(2S)-2-phenylglycinol

(1R,2R)-1-tert-Butyl-1-thioxo-1λ⁵-phospholane-2-carboxylic acid

1-tert-butyl-phospholane 1-sulfide

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