(2S,2'R,5'S,1''S)-2-Benzyloxycarbonylamino-3-[5'-(1''-tert-butoxycarbonylaminoethyl)tetrahydrofuran-2'-carbamoyl] methyl propionate

Base Information

Chemical Name:(2S,2'R,5'S,1''S)-2-Benzyloxycarbonylamino-3-[5'-(1''-tert-butoxycarbonylaminoethyl)tetrahydrofuran-2'-carbamoyl] methyl propionate
CAS No.:264198-10-9
Molecular Formula:C₂₄H₃₅N₃O₈
Molecular Weight:493.557
Hs Code.:

Synonyms:(2S,2'R,5'S,1''S)-2-Benzyloxycarbonylamino-3-[5'-(1''-tert-butoxycarbonylaminoethyl)tetrahydrofuran-2'-carbamoyl] methyl propionate

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Chemical Property of (2S,2'R,5'S,1''S)-2-Benzyloxycarbonylamino-3-[5'-(1''-tert-butoxycarbonylaminoethyl)tetrahydrofuran-2'-carbamoyl] methyl propionate

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Technology Process of (2S,2'R,5'S,1''S)-2-Benzyloxycarbonylamino-3-[5'-(1''-tert-butoxycarbonylaminoethyl)tetrahydrofuran-2'-carbamoyl] methyl propionate

There total 1 articles about (2S,2'R,5'S,1''S)-2-Benzyloxycarbonylamino-3-[5'-(1''-tert-butoxycarbonylaminoethyl)tetrahydrofuran-2'-carbamoyl] methyl propionate 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: 84.0%

: 35761-27-4,96192-93-7
methyl (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoate hydrochloride

: 259091-45-7
(2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylic acid

: 264198-10-9
(2S,2'R,5'S,1''S)-2-Benzyloxycarbonylamino-3-[5'-(1''-tert-butoxycarbonylaminoethyl)tetrahydrofuran-2'-carbamoyl] methyl propionate

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 16h;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

: 264198-10-9
(2S,2'R,5'S,1''S)-2-Benzyloxycarbonylamino-3-[5'-(1''-tert-butoxycarbonylaminoethyl)tetrahydrofuran-2'-carbamoyl] methyl propionate

: 294664-69-0
(S)-3-{[(2R,5S)-5-((S)-1-Amino-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-2-benzyloxycarbonylamino-propionic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

: 264198-10-9
(2S,2'R,5'S,1''S)-2-Benzyloxycarbonylamino-3-[5'-(1''-tert-butoxycarbonylaminoethyl)tetrahydrofuran-2'-carbamoyl] methyl propionate

: (S)-3-({(2R,5S)-5-[(S)-1-(2-Amino-acetylamino)-ethyl]-tetrahydro-furan-2-carbonyl}-amino)-2-benzyloxycarbonylamino-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: TFA / CH₂Cl₂ / 2 h / 20 °C

2: 350 mg / HOBt; EDC; iPr₂NEt / tetrahydrofuran / 18 h / 20 °C

3: TFA / CH₂Cl₂ / 2 h / 20 °C

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Deacylation / 2: Acylation / 3: Deacylation;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z