(2-{(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[2-cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid benzyl ester

Base Information

• Chemical Name: (2-{(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[2-cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid benzyl ester
• CAS No.: 727708-90-9
• Molecular Formula: C₄₁H₄₆N₃O₅PSi
• Molecular Weight: 719.893

Synonyms:(2-{(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[2-cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid benzyl ester

Chemical Property of (2-{(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[2-cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid benzyl ester

Chemical Property:

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Technology Process of (2-{(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[2-cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid benzyl ester

There total 4 articles about (2-{(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[2-cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid benzyl ester 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: 59.0%

cyanomethylene triphenylphosphorane (16640-68-9) + (2S,4R)-1-(2-Benzyloxycarbonylamino-acetyl)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-2-carboxylic acid (727708-88-5) → (2-{(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[2-cyano-2-(triphenyl-λ5-phosphanylidene)-acetyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid benzyl ester (727708-90-9)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1055/s-2004-822906

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2-{(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[2-cyano-2-(triphenyl-λ5-phosphanylidene)-acetyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid benzyl ester (727708-90-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / Et₃N / CH₂Cl₂

2: 95 percent / DBU / acetonitrile

3: 96 percent / NaOH / methanol

4: 59 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂

With dmap; sodium hydroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1055/s-2004-822906

Reference yield:

carbobenzyloxyglycinesuccinimido ester (60341-62-0) → (2-{(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[2-cyano-2-(triphenyl-λ5-phosphanylidene)-acetyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid benzyl ester (727708-90-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / Et₃N / CH₂Cl₂

2: 95 percent / DBU / acetonitrile

3: 96 percent / NaOH / methanol

4: 59 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂

With dmap; sodium hydroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1055/s-2004-822906

upstream raw materials:

cyanomethylene triphenylphosphorane

(2S,4R)-1-(2-Benzyloxycarbonylamino-acetyl)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-2-carboxylic acid

carbobenzyloxyglycinesuccinimido ester

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

3-(benzyloxycarbonylamino-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-1-carboxylic acid methyl ester

[(2S,4R)-1-(2-Benzyloxycarbonylamino-acetyl)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-oxo-acetic acid methyl ester

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