3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid trityloxy-amide

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Chemical Name:3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid trityloxy-amide
CAS No.:310890-70-1
Molecular Formula:C₃₈H₄₄N₂O₈S
Molecular Weight:688.842
Hs Code.:

Synonyms:3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid trityloxy-amide

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Chemical Property of 3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid trityloxy-amide

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Technology Process of 3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid trityloxy-amide

There total 10 articles about 3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid trityloxy-amide 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: 54.0%

: 31938-11-1
O-tritylhydroxylamine

: 310890-64-3
3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid

: 310890-70-1
3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid trityloxy-amide

Guidance literature:: With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran;
DOI:10.1016/S0040-4020(00)00687-6

Reference yield:

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

: 310890-70-1
3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid trityloxy-amide

Guidance literature:: Multi-step reaction with 10 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: 88 percent / Et₃N / CH₂Cl₂ / 16 h / 0 - 20 °C

7.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 0 °C

8.1: 4 Angstroem molecular sieves; N-methylmorpholine; TPAP / CH₂Cl₂

9.1: 94 mg / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 3 h

10.1: 54 percent / EDC; HOBT; N-methylmorpholine / tetrahydrofuran

With 4-methyl-morpholine; sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 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; water; toluene; tert-butyl alcohol; 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 / 8.1: Oxidation / 9.1: Oxidation / 10.1: Condensation;
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

: 310890-70-1
3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid trityloxy-amide

Guidance literature:: Multi-step reaction with 9 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: 88 percent / Et₃N / CH₂Cl₂ / 16 h / 0 - 20 °C

6.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 0 °C

7.1: 4 Angstroem molecular sieves; N-methylmorpholine; TPAP / CH₂Cl₂

8.1: 94 mg / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 3 h

9.1: 54 percent / EDC; HOBT; N-methylmorpholine / tetrahydrofuran

With 4-methyl-morpholine; sodium chlorite; sodium dihydrogenphosphate; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 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; water; toluene; tert-butyl alcohol; 1.1: Substitution / 2.1: Reduction / 3.1: Condensation / 3.2: Substitution / 4.1: Catalytic hydrogenation / 5.1: Condensation / 6.1: ether cleavage / 7.1: Oxidation / 8.1: Oxidation / 9.1: Condensation;
DOI:10.1016/S0040-4020(00)00687-6