(3S,4R,2'S,1''S,2'''S)-3-(2'-acetylamino-3'-tert-butoxy-propionylamino)-1-[5''-benzyloxycarbonylamino-1''-(2'''-tert-butoxycarbonyl-pyrrolidine-1'''-carbonyl)-pentyl]-2-oxo-piperidine-4-carboxylic acid

Base Information

• Chemical Name: (3S,4R,2'S,1''S,2'''S)-3-(2'-acetylamino-3'-tert-butoxy-propionylamino)-1-[5''-benzyloxycarbonylamino-1''-(2'''-tert-butoxycarbonyl-pyrrolidine-1'''-carbonyl)-pentyl]-2-oxo-piperidine-4-carboxylic acid
• CAS No.: 862473-36-7
• Molecular Formula: C₃₈H₅₇N₅O₁₁
• Molecular Weight: 759.897
• Mol file: 862473-36-7.mol

Synonyms:(3S,4R,2'S,1''S,2'''S)-3-(2'-acetylamino-3'-tert-butoxy-propionylamino)-1-[5''-benzyloxycarbonylamino-1''-(2'''-tert-butoxycarbonyl-pyrrolidine-1'''-carbonyl)-pentyl]-2-oxo-piperidine-4-carboxylic acid

Chemical Property of (3S,4R,2'S,1''S,2'''S)-3-(2'-acetylamino-3'-tert-butoxy-propionylamino)-1-[5''-benzyloxycarbonylamino-1''-(2'''-tert-butoxycarbonyl-pyrrolidine-1'''-carbonyl)-pentyl]-2-oxo-piperidine-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,2'S,1''S,2'''S)-3-(2'-acetylamino-3'-tert-butoxy-propionylamino)-1-[5''-benzyloxycarbonylamino-1''-(2'''-tert-butoxycarbonyl-pyrrolidine-1'''-carbonyl)-pentyl]-2-oxo-piperidine-4-carboxylic acid

There total 12 articles about (3S,4R,2'S,1''S,2'''S)-3-(2'-acetylamino-3'-tert-butoxy-propionylamino)-1-[5''-benzyloxycarbonylamino-1''-(2'''-tert-butoxycarbonyl-pyrrolidine-1'''-carbonyl)-pentyl]-2-oxo-piperidine-4-carboxylic acid 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: 75.0%

(2S,2'S,3''S,4''S,2'''S)-1-{2'-[3''-(2'''-acetylamino-3'''-tert-butoxy-propionylamino)-2''-oxo-4''-vinyl-piperidin-1''-yl]-6'-benzyloxycarbonylamino-hexanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester (862473-35-6) → (3S,4R,2'S,1''S,2'''S)-3-(2'-acetylamino-3'-tert-butoxy-propionylamino)-1-[5''-benzyloxycarbonylamino-1''-(2'''-tert-butoxycarbonyl-pyrrolidine-1'''-carbonyl)-pentyl]-2-oxo-piperidine-4-carboxylic acid (862473-36-7)

Guidance literature:

With sodium periodate; ruthenium trichloride; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 24h;

DOI:10.1021/jo050736k

Reference yield:

(2S,2'S,3''S,4''S)-1-[2'-(3''-amino-2''-oxo-4''-vinyl-piperidin-1''-yl)-6'-benzyloxycarbonylamino-hexanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester (862473-27-6) → (3S,4R,2'S,1''S,2'''S)-3-(2'-acetylamino-3'-tert-butoxy-propionylamino)-1-[5''-benzyloxycarbonylamino-1''-(2'''-tert-butoxycarbonyl-pyrrolidine-1'''-carbonyl)-pentyl]-2-oxo-piperidine-4-carboxylic acid (862473-36-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / EDC; HOBt / CH₂Cl₂ / 24 h / 20 °C

2: 96 percent / diethylamine / tetrahydrofuran / 3.25 h / 0 - 20 °C

3: 86 percent / triethylamine / DMAP / CH₂Cl₂ / 24 h / 20 °C

4: 75 percent / sodium metaperiodate / ruthenium trichloride hydrate / H₂O; CCl₄; acetonitrile / 24 h / 20 °C

With sodium periodate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; triethylamine; dmap; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo050736k

Reference yield:

(2S,2'S,3''S,4''S)-1-[6'-benzyloxycarbonylamino-2'-(3''-tert-butoxycarbonylamino-2''-oxo-4''-vinyl-piperidin-1''-yl)-hexanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester (862473-26-5) → (3S,4R,2'S,1''S,2'''S)-3-(2'-acetylamino-3'-tert-butoxy-propionylamino)-1-[5''-benzyloxycarbonylamino-1''-(2'''-tert-butoxycarbonyl-pyrrolidine-1'''-carbonyl)-pentyl]-2-oxo-piperidine-4-carboxylic acid (862473-36-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 67 percent / aq. HCl / ethyl acetate / 3 h / -50 - 0 °C

2: 85 percent / EDC; HOBt / CH₂Cl₂ / 24 h / 20 °C

3: 96 percent / diethylamine / tetrahydrofuran / 3.25 h / 0 - 20 °C

4: 86 percent / triethylamine / DMAP / CH₂Cl₂ / 24 h / 20 °C

5: 75 percent / sodium metaperiodate / ruthenium trichloride hydrate / H₂O; CCl₄; acetonitrile / 24 h / 20 °C

With hydrogenchloride; sodium periodate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; triethylamine; dmap; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1021/jo050736k

upstream raw materials:

(2S,2'S,3''S,4''S,2'''S)-1-{2'-[3''-(2'''-acetylamino-3'''-tert-butoxy-propionylamino)-2''-oxo-4''-vinyl-piperidin-1''-yl]-6'-benzyloxycarbonylamino-hexanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester

(2S,2'S,3''S,4''S)-1-[2'-(3''-amino-2''-oxo-4''-vinyl-piperidin-1''-yl)-6'-benzyloxycarbonylamino-hexanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

(2S,2'S,3''S,4''S)-1-[6'-benzyloxycarbonylamino-2'-(3''-tert-butoxycarbonylamino-2''-oxo-4''-vinyl-piperidin-1''-yl)-hexanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

(4S,1'S,1'''S,2''''S)-4-(1'-{2''-[5'''-benzyloxycarbonylamino-1'''-(2''''-tert-butoxycarbonyl-pyrrolidine-1''''-carbonyl)-pentylamino]-ethyl}-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester