2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide

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Chemical Name:2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide
CAS No.:310890-54-1
Molecular Formula:C₂₃H₃₆N₂O₆
Molecular Weight:436.549
Hs Code.:

Synonyms:2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide

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Chemical Property of 2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide

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Technology Process of 2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide

There total 7 articles about 2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide 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: 87.0%

: 310890-48-3
2(S)-acetylamino-N-[5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide

: 310890-54-1
2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0040-4020(00)00687-6

Reference yield:

: 99315-76-1
(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone

: 310890-54-1
2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 98 percent / CuI; DMS / tetrahydrofuran / -78 - 0 °C

2.1: 69 percent / trisyl azode / tetrahydrofuran / 0.5 h / -78 °C

3.1: 20 percent / Dibal-H / tetrahydrofuran; toluene / 11 h / -60 °C

4.1: 4 Angstroem molecular sieves; Et₃N / CH₂Cl₂ / 36 h / 20 °C

4.2: 53 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂ / 2 h / 0 - 20 °C

5.1: 96 percent / H₂ / Pd/C / ethanol / 20 h

6.1: 66 percent / EDC; HOBT; N-methylmorpholine / tetrahydrofuran / 15 h

7.1: 87 percent / TBAF; AcOH / tetrahydrofuran / 0 °C

With 4-methyl-morpholine; copper(l) iodide; 2,3-dimercapto-succinic acid; 4 A molecular sieve; 2,4,6-Triisopropylbenzenesulfonyl azide; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene; 1.1: Addition / 2.1: Substitution / 3.1: Reduction / 4.1: Condensation / 4.2: Substitution / 5.1: Catalytic hydrogenation / 6.1: Condensation / 7.1: ether cleavage;
DOI:10.1016/S0040-4020(00)00687-6

Reference yield:

: 310889-88-4
5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-dihydro-furan-2-one

: 310890-54-1
2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 69 percent / trisyl azode / tetrahydrofuran / 0.5 h / -78 °C

2.1: 20 percent / Dibal-H / tetrahydrofuran; toluene / 11 h / -60 °C

3.1: 4 Angstroem molecular sieves; Et₃N / CH₂Cl₂ / 36 h / 20 °C

3.2: 53 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂ / 2 h / 0 - 20 °C

4.1: 96 percent / H₂ / Pd/C / ethanol / 20 h

5.1: 66 percent / EDC; HOBT; N-methylmorpholine / tetrahydrofuran / 15 h

6.1: 87 percent / TBAF; AcOH / tetrahydrofuran / 0 °C

With 4-methyl-morpholine; 4 A molecular sieve; 2,4,6-Triisopropylbenzenesulfonyl azide; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene; 1.1: Substitution / 2.1: Reduction / 3.1: Condensation / 3.2: Substitution / 4.1: Catalytic hydrogenation / 5.1: Condensation / 6.1: ether cleavage;
DOI:10.1016/S0040-4020(00)00687-6