(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

Base Information

• Chemical Name: (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
• CAS No.: 862473-26-5
• Molecular Formula: C₃₅H₅₂N₄O₈
• Molecular Weight: 656.82
• Mol file: 862473-26-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 11 articles about (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 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: 71.0%

(2S,2'S,3''S,2'''S)-1-{6'-benzyloxycarbonylamino-2'-[[3'''-(tert-butoxycarbonylamino-carboxy-methyl)-pent-4'''-enyl]-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-hexanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester (862473-25-4) → (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)

Guidance literature:

(2S,2'S,3''S,2'''S)-1-{6'-benzyloxycarbonylamino-2'-[[3'''-(tert-butoxycarbonylamino-carboxy-methyl)-pent-4'''-enyl]-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-hexanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester; With diethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 6.25h;

With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; 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)-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)

Guidance literature:

Multi-step reaction with 4 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

With jones reagent; sodium tris(acetoxy)borohydride; sodium carbonate; diethylamine; In tetrahydrofuran; water; acetone; 3.1: Jones oxidation;

DOI:10.1021/jo050736k

Reference yield:

(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 (862473-23-2) → (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)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

2.1: 57 percent / Jones reagent / acetone / 3 h / 20 °C

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

3.2: 71 percent / TBTU; HOBt; DIEA / dimethylformamide / 24 h / 20 °C

With jones reagent; sodium carbonate; diethylamine; In tetrahydrofuran; water; acetone; 2.1: Jones oxidation;

DOI:10.1021/jo050736k

upstream raw materials:

(2S,2'S,3''S,2'''S)-1-{6'-benzyloxycarbonylamino-2'-[[3'''-(tert-butoxycarbonylamino-carboxy-methyl)-pent-4'''-enyl]-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-hexanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester

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

(4S,1'S,1'''S,2''''S)-4-(1'-{2''-[[5'''-benzyloxycarbonylamino-1'''-(2''''-tert-butoxycarbonyl-pyrrolidine-1''''-carbonyl)-pentyl]-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-ethyl}-allyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Downstream 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

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

(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

(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