(2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine

Base Information

• Chemical Name: (2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine
• CAS No.: 178158-98-0
• Molecular Formula: C₃₂H₂₈NO₄PS
• Molecular Weight: 553.618
• Mol file: 178158-98-0.mol

Synonyms:(2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine

Chemical Property of (2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine

There total 16 articles about (2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-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: 100.0%

(2S,4S)-4-diphenylphosphinothioyl-proline hydrochloride + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine (178158-98-0)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone;

DOI:10.1021/jo0158231

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine (178158-98-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 90 percent / EDC; HOBt; Et₃N / CH₂Cl₂ / 24 h / 20 °C

2.1: LiBH₄ / tetrahydrofuran / 16 h / 20 °C

3.1: 61 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

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

4.2: 65 percent / S₈ / tetrahydrofuran / 2 h / 20 °C

5.1: 75 percent / HCl / H₂O / 2 h / Heating

6.1: 100 percent / NaHCO₃ / acetone; H₂O

With hydrogenchloride; lithium borohydride; sodium hydrogencarbonate; benzotriazol-1-ol; sodium amide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1021/jo0158231

Reference yield:

(2S,4R)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-isopropyl)methyl]amino]carbonyl]-4-hydroxyl-pyrrolidine (251939-57-8) → (2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine (178158-98-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 61 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

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

2.2: 65 percent / S₈ / tetrahydrofuran / 2 h / 20 °C

3.1: 75 percent / HCl / H₂O / 2 h / Heating

4.1: 100 percent / NaHCO₃ / acetone; H₂O

With hydrogenchloride; sodium hydrogencarbonate; sodium amide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1021/jo0158231

upstream raw materials:

(2S,4S)-4-(Diphenyl-phosphinothioyl)-2-formyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-N-tert-butyloxycarbonyl-2-[[N-[hydroxymethyl-((S)-isopropyl)methyl]amino]carbonyl]-4-hydroxyl-pyrrolidine