Cyclopentanecarboxylic acid, 1-[[methoxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphin yl]methyl]-, 1,1-dimethylethyl ester, (1R)-

Base Information

• Chemical Name: Cyclopentanecarboxylic acid, 1-[[methoxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphin yl]methyl]-, 1,1-dimethylethyl ester, (1R)-
• CAS No.: 182211-11-6
• Molecular Formula: C₂₈H₃₈NO₆P
• Molecular Weight: 515.587
• Mol file: 182211-11-6.mol

Synonyms:

Chemical Property of Cyclopentanecarboxylic acid, 1-[[methoxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphin yl]methyl]-, 1,1-dimethylethyl ester, (1R)-

Chemical Property:

Purity/Quality:

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Technology Process of Cyclopentanecarboxylic acid, 1-[[methoxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphin yl]methyl]-, 1,1-dimethylethyl ester, (1R)-

There total 3 articles about Cyclopentanecarboxylic acid, 1-[[methoxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphin yl]methyl]-, 1,1-dimethylethyl ester, (1R)- 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)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)phosphinic acid (118636-74-1) → 1-[((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-methoxy-phosphinoylmethyl]-cyclopentanecarboxylic acid tert-butyl ester (182211-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / ethyl acetate; methanol

2: 1.) LDA / 1.) THF, -78 deg C, 2.) THF, -78 deg C -> rt

With lithium diisopropyl amide; In methanol; ethyl acetate;

DOI:10.1016/0960-894X(96)00297-1

Reference yield:

t-Butyl 1-(Hydroxymethyl)cyclopentanecarboxylate (137613-90-2) → 1-[((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-methoxy-phosphinoylmethyl]-cyclopentanecarboxylic acid tert-butyl ester (182211-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / pyridine; CH₂Cl₂ / -78 - 0 °C

2: 1.) LDA / 1.) THF, -78 deg C, 2.) THF, -78 deg C -> rt

With lithium diisopropyl amide; In pyridine; dichloromethane;

DOI:10.1016/0960-894X(96)00297-1

Reference yield:

methyl (1R)-1-<(benzyloxycarbonyl)amino>-2-phenylethyl phosphinate (174850-07-8,174850-08-9,129312-69-2) + t-Butyl 1-[(trifluoromethanesulfonyl)oxy]methylcyclopentanecarboxylate (174767-44-3) → 1-[((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-methoxy-phosphinoylmethyl]-cyclopentanecarboxylic acid tert-butyl ester (182211-11-6)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -78 deg C, 2.) THF, -78 deg C -> rt;

DOI:10.1016/0960-894X(96)00297-1

upstream raw materials:

methyl (1R)-1-<(benzyloxycarbonyl)amino>-2-phenylethyl phosphinate

t-Butyl 1-[(trifluoromethanesulfonyl)oxy]methylcyclopentanecarboxylate

((R)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)phosphinic acid

t-Butyl 1-(Hydroxymethyl)cyclopentanecarboxylate

Downstream raw materials:

1-[((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-hydroxy-phosphinoylmethyl]-cyclopentanecarboxylic acid

N-[[1-[[hydroxy[2-phenyl-1(R)-[[2(S)-[(methylsulfonyl)amino]-1-oxo-6-[[(phenylmethoxy)carbonyl]amino]hexyl]amino]ethyl]phosphinyl]methyl]cyclopentyl]carbonyl]-L-tryptophan

(S)-2-({1-[((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-hydroxy-phosphinoylmethyl]-cyclopentanecarbonyl}-amino)-3-(1H-indol-3-yl)-propionic acid methyl ester

(S)-2-({1-[((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-hydroxy-phosphinoylmethyl]-cyclopentanecarbonyl}-amino)-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester

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