(2S,2'RS,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

Base Information

Chemical Name:(2S,2'RS,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate
CAS No.:264197-98-0
Molecular Formula:C₃₀H₄₈N₄O₁₀S
Molecular Weight:656.798
Hs Code.:

(2S,2'RS,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

Synonyms:(2S,2'RS,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,2'RS,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (2S,2'RS,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

There total 8 articles about (2S,2'RS,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino 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: 61.0%

: 264197-96-8
(2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2-carboxylic acid

: (S)-3-Amino-2-(butane-1-sulfonylamino)-propionic acid methyl ester; compound with trifluoro-acetic acid

: 264197-98-0
(2S,2'RS,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 18h;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

: 7733-29-1,199924-46-4
Z-Orn(Boc)-OH

: 264197-98-0
(2S,2'RS,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

Guidance literature:: Multi-step reaction with 8 steps

1.1: N,N'-diisopropyl carbodiimide / CH₂Cl₂ / 4 h / 20 °C

2.1: Mg / diethyl ether / 1 h / Heating

2.2: LiCl; CuCN / tetrahydrofuran / 0.25 h / -40 °C

2.3: 3.72 g / tetrahydrofuran / 0.67 h / -78 - -5 °C

3.1: 46 percent / L-Selectride / tetrahydrofuran / 1 h / -100 - -70 °C

4.1: MCPBA / CH₂Cl₂ / 3.5 h / 20 °C

5.1: 670 mg / PPTS / CH₂Cl₂ / 12 h / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -60 - 0 °C

7.1: 3.37 g / aq. NaClO₂; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 12 h / 20 °C

8.1: 61 percent / iPr₂NEt; EDC; HOBt / tetrahydrofuran / 18 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; pyridinium p-toluenesulfonate; L-Selectride; benzotriazol-1-ol; magnesium; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; diisopropyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol; 1.1: Esterification / 2.1: Metallation / 2.2: Substitution / 2.3: Acylation / 3.1: Reduction / 4.1: Epoxidation / 5.1: Ring cleavage / 6.1: Oxidation / 7.1: Oxidation / 8.1: Acylation;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

: 264197-97-9
[(S)-4-Benzyloxycarbonylamino-4-((R)-5-formyl-tetrahydro-furan-2-yl)-butyl]-carbamic acid tert-butyl ester

: 264197-98-0
(2S,2'RS,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

Guidance literature:: Multi-step reaction with 2 steps

1: 3.37 g / aq. NaClO₂; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 12 h / 20 °C

2: 61 percent / iPr₂NEt; EDC; HOBt / tetrahydrofuran / 18 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; tert-butyl alcohol; 1: Oxidation / 2: Acylation;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z