(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

Base Information

• Chemical Name: (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
• CAS No.: 862473-35-6
• Molecular Formula: C₃₉H₅₉N₅O₉
• Molecular Weight: 741.926
• Mol file: 862473-35-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 14 articles about (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 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: 86.0%

(2S,2'S,3''S,4''S,2'''S)-1-{2'-[3''-(2'''-amino-3'''-tert-butoxy-propionylamino)-2''-oxo-4''-vinyl-piperidin-1''-yl]-6'-benzyloxycarbonylamino-hexanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester (862473-34-5) + acetic anhydride (108-24-7) → (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)

Guidance literature:

With triethylamine; dmap; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo050736k

Reference yield:

(4S,1'S)-2,2-dimethyl-4-[1'-(2''-oxoethyl)allyl]oxazolidine-3-carboxylic acid tert-butyl ester (862473-08-3) → (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)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 74 percent / sodium triacetoxyborohydride / tetrahydrofuran / 15 h / 20 °C

2.1: 92 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

3.1: 57 percent / Jones reagent / acetone / 3 h / 20 °C

4.1: diethylamine / tetrahydrofuran / 6.25 h / 0 - 20 °C

4.2: 71 percent / TBTU; HOBt; DIEA / dimethylformamide / 24 h / 20 °C

5.1: 67 percent / aq. HCl / ethyl acetate / 3 h / -50 - 0 °C

6.1: 85 percent / EDC; HOBt / CH₂Cl₂ / 24 h / 20 °C

7.1: 96 percent / diethylamine / tetrahydrofuran / 3.25 h / 0 - 20 °C

8.1: 86 percent / triethylamine / DMAP / CH₂Cl₂ / 24 h / 20 °C

With hydrogenchloride; jones reagent; sodium tris(acetoxy)borohydride; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; triethylamine; dmap; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; 3.1: Jones oxidation;

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) → (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)

Guidance literature:

Multi-step reaction with 3 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

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; triethylamine; dmap; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo050736k

upstream raw materials:

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

acetic anhydride

(4S,1'S)-2,2-dimethyl-4-[1'-(2''-oxoethyl)allyl]oxazolidine-3-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

Downstream raw materials:

(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