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

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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
CAS No.:310890-64-3
Molecular Formula:C₁₉H₂₉NO₈S
Molecular Weight:431.507
Hs Code.:

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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

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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

There total 9 articles about 3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid 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:

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

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

Guidance literature:: Multi-step reaction with 9 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

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; acetic acid; 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;
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

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

Guidance literature:: Multi-step reaction with 8 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

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; acetic acid; 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;
DOI:10.1016/S0040-4020(00)00687-6

Reference yield:

: 310889-92-0
3(S)-azido-5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-dihydro-furan-2-one

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

Guidance literature:: Multi-step reaction with 7 steps

1.1: 20 percent / Dibal-H / tetrahydrofuran; toluene / 11 h / -60 °C

2.1: 4 Angstroem molecular sieves; Et₃N / CH₂Cl₂ / 36 h / 20 °C

2.2: 53 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 96 percent / H₂ / Pd/C / ethanol / 20 h

4.1: 88 percent / Et₃N / CH₂Cl₂ / 16 h / 0 - 20 °C

5.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 0 °C

6.1: 4 Angstroem molecular sieves; N-methylmorpholine; TPAP / CH₂Cl₂

7.1: 94 mg / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 3 h

With 4-methyl-morpholine; sodium chlorite; sodium dihydrogenphosphate; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; tert-butyl alcohol; 1.1: Reduction / 2.1: Condensation / 2.2: Substitution / 3.1: Catalytic hydrogenation / 4.1: Condensation / 5.1: ether cleavage / 6.1: Oxidation / 7.1: Oxidation;
DOI:10.1016/S0040-4020(00)00687-6