(2S,2'S,3''S,4''S,2'''S)-1-(6'-benzyloxycarbonylamino-2'-{3''-[3'''-tert-butoxy-2'''-(9H-fluoren-9''''-ylmethoxycarbonylamino)-propionylamino]-2''-oxo-4''-vinyl-piperidin-1''-yl}-hexanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,2'S,3''S,4''S,2'''S)-1-(6'-benzyloxycarbonylamino-2'-{3''-[3'''-tert-butoxy-2'''-(9H-fluoren-9''''-ylmethoxycarbonylamino)-propionylamino]-2''-oxo-4''-vinyl-piperidin-1''-yl}-hexanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester
CAS No.:862473-33-4
Molecular Formula:C₅₂H₆₇N₅O₁₀
Molecular Weight:922.131
Hs Code.:

(2S,2'S,3''S,4''S,2'''S)-1-(6'-benzyloxycarbonylamino-2'-{3''-[3'''-tert-butoxy-2'''-(9H-fluoren-9''''-ylmethoxycarbonylamino)-propionylamino]-2''-oxo-4''-vinyl-piperidin-1''-yl}-hexanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Synonyms:(2S,2'S,3''S,4''S,2'''S)-1-(6'-benzyloxycarbonylamino-2'-{3''-[3'''-tert-butoxy-2'''-(9H-fluoren-9''''-ylmethoxycarbonylamino)-propionylamino]-2''-oxo-4''-vinyl-piperidin-1''-yl}-hexanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

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Chemical Property of (2S,2'S,3''S,4''S,2'''S)-1-(6'-benzyloxycarbonylamino-2'-{3''-[3'''-tert-butoxy-2'''-(9H-fluoren-9''''-ylmethoxycarbonylamino)-propionylamino]-2''-oxo-4''-vinyl-piperidin-1''-yl}-hexanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

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Technology Process of (2S,2'S,3''S,4''S,2'''S)-1-(6'-benzyloxycarbonylamino-2'-{3''-[3'''-tert-butoxy-2'''-(9H-fluoren-9''''-ylmethoxycarbonylamino)-propionylamino]-2''-oxo-4''-vinyl-piperidin-1''-yl}-hexanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

There total 12 articles about (2S,2'S,3''S,4''S,2'''S)-1-(6'-benzyloxycarbonylamino-2'-{3''-[3'''-tert-butoxy-2'''-(9H-fluoren-9''''-ylmethoxycarbonylamino)-propionylamino]-2''-oxo-4''-vinyl-piperidin-1''-yl}-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: 85.0%

: 862473-27-6
(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

: 71989-33-8
Fmoc-Ser(tBu)-OH

: 862473-33-4
(2S,2'S,3''S,4''S,2'''S)-1-(6'-benzyloxycarbonylamino-2'-{3''-[3'''-tert-butoxy-2'''-(9H-fluoren-9''''-ylmethoxycarbonylamino)-propionylamino]-2''-oxo-4''-vinyl-piperidin-1''-yl}-hexanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/jo050736k

Reference yield:

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

: 862473-33-4
(2S,2'S,3''S,4''S,2'''S)-1-(6'-benzyloxycarbonylamino-2'-{3''-[3'''-tert-butoxy-2'''-(9H-fluoren-9''''-ylmethoxycarbonylamino)-propionylamino]-2''-oxo-4''-vinyl-piperidin-1''-yl}-hexanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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

With hydrogenchloride; jones reagent; sodium tris(acetoxy)borohydride; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; 3.1: Jones oxidation;
DOI:10.1021/jo050736k

Reference yield:

: 862473-26-5
(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

: 862473-33-4
(2S,2'S,3''S,4''S,2'''S)-1-(6'-benzyloxycarbonylamino-2'-{3''-[3'''-tert-butoxy-2'''-(9H-fluoren-9''''-ylmethoxycarbonylamino)-propionylamino]-2''-oxo-4''-vinyl-piperidin-1''-yl}-hexanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

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

With hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; ethyl acetate;
DOI:10.1021/jo050736k