(2S,4S)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-methoxycarbonyl)methyl]amino]carbonyl]-4-diphenylphosphinothioyl-pyrrolidine

Base Information

• Chemical Name: (2S,4S)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-methoxycarbonyl)methyl]amino]carbonyl]-4-diphenylphosphinothioyl-pyrrolidine
• CAS No.: 369366-66-5
• Molecular Formula: C₂₆H₃₃N₂O₆PS
• Molecular Weight: 532.598
• Mol file: 369366-66-5.mol

Synonyms:(2S,4S)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-methoxycarbonyl)methyl]amino]carbonyl]-4-diphenylphosphinothioyl-pyrrolidine

Chemical Property of (2S,4S)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-methoxycarbonyl)methyl]amino]carbonyl]-4-diphenylphosphinothioyl-pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (2S,4S)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-methoxycarbonyl)methyl]amino]carbonyl]-4-diphenylphosphinothioyl-pyrrolidine

There total 1 articles about (2S,4S)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-methoxycarbonyl)methyl]amino]carbonyl]-4-diphenylphosphinothioyl-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: 96.0%

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) + (2S,4S)-N-tert-butyloxycarbonyl-4-diphenylphosphinothioyl-proline (178158-99-1) → (2S,4S)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-methoxycarbonyl)methyl]amino]carbonyl]-4-diphenylphosphinothioyl-pyrrolidine (369366-66-5)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo0158231

Reference yield: 93.0%

(2S,4S)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-methoxycarbonyl)methyl]amino]carbonyl]-4-diphenylphosphinothioyl-pyrrolidine (369366-66-5) → (2S,4'R,4S)-N-tert-butyloxycarbonyl-2-(4,5-dihydro-4-methoxycarbonyl-1,3-oxazole-2-yl)-4-diphenylphosphinothioyl-pyrrolidine

Guidance literature:

With Burgess Reagent; In tetrahydrofuran; for 3h; Heating;

DOI:10.1021/jo0158231

Reference yield:

(2S,4S)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-methoxycarbonyl)methyl]amino]carbonyl]-4-diphenylphosphinothioyl-pyrrolidine (369366-66-5) → (S)-2-((2S,4S)-1-tert-Butoxycarbonyl-4-diphenylphosphanyl-pyrrolidin-2-yl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Burgess reagent / tetrahydrofuran / 3 h / Heating

2: Raney nickel / acetonitrile / 20 °C

With Burgess Reagent; nickel; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo0158231

upstream raw materials:

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride

(2S,4S)-N-tert-butyloxycarbonyl-4-diphenylphosphinothioyl-proline