(2S,4'R,4R)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-(methylsulfonyl)oxyl-pyrrolidine

Base Information

• Chemical Name: (2S,4'R,4R)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-(methylsulfonyl)oxyl-pyrrolidine
• CAS No.: 369366-61-0
• Molecular Formula: C₁₆H₂₈N₂O₆S
• Molecular Weight: 376.474

Synonyms:(2S,4'R,4R)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-(methylsulfonyl)oxyl-pyrrolidine

Chemical Property of (2S,4'R,4R)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-(methylsulfonyl)oxyl-pyrrolidine

Chemical Property:

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Technology Process of (2S,4'R,4R)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-(methylsulfonyl)oxyl-pyrrolidine

There total 1 articles about (2S,4'R,4R)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-(methylsulfonyl)oxyl-pyrrolidine 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:

(R)-2-amino-3-methylbutanol (4276-09-9,473-75-6) → (2S,4'R,4R)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-(methylsulfonyl)oxyl-pyrrolidine (369366-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 36 percent / EDC; HOBt / CH₂Cl₂ / 24 h / 20 °C

2: 54 percent / Et₃N / CH₂Cl₂ / 20 °C

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane;

DOI:10.1021/jo0158231

Reference yield: 39.0%

(2S,4'R,4R)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-(methylsulfonyl)oxyl-pyrrolidine (369366-61-0) + diphenylphosphane (829-85-6) → (2S,4'R,4S)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-diphenylphosphinothioyl-pyrrolidine (369366-57-4)

Guidance literature:

(2S,4'R,4R)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-(methylsulfonyl)oxyl-pyrrolidine; diphenylphosphane; With sodium amide; In tetrahydrofuran; at 20 ℃; for 12h;

With sulfur; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;

DOI:10.1021/jo0158231

Reference yield:

(2S,4'R,4R)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-(methylsulfonyl)oxyl-pyrrolidine (369366-61-0) → (2S,4S)-4-Diphenylphosphanyl-2-((R)-4-isopropyl-4,5-dihydro-oxazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaNH₂ / tetrahydrofuran / 12 h / 20 °C

1.2: 39 percent / S₈ / tetrahydrofuran / 2 h / 20 °C

2.1: Raney nickel / acetonitrile / 20 °C

With sodium amide; nickel; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo0158231

upstream raw materials:

(R)-2-amino-3-methylbutanol

Downstream raw materials:

(2S,4'R,4S)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-isopropyl-1,3-oxazole-2-yl)-4-diphenylphosphinothioyl-pyrrolidine

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