ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate

Base Information

Chemical Name:ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate
CAS No.:1196491-09-4
Molecular Formula:C₂₄H₃₆N₂O₈S
Molecular Weight:512.624
Hs Code.:

ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate

Synonyms:ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate

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Chemical Property of ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate

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Technology Process of ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate

There total 19 articles about ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate 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: 95.0%

: 1196491-05-0
ethyl (3aR,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}-3a,6,7,7a-tetrahydro-1,3-benzodioxole-4-carboxylate

: 1196491-09-4
ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate

Guidance literature:: With hydrogen; 5% rhodium on alumina; In ethanol; at 20 ℃; for 144h; under 2844.39 Torr;

Reference yield:

: 1196491-05-0
ethyl (3aR,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}-3a,6,7,7a-tetrahydro-1,3-benzodioxole-4-carboxylate

: 1196491-09-4
ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate

: ethyl (3aR,4S,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate

Guidance literature:: With Rh/Al₂O₃; hydrogen; In ethanol; at 20 ℃; for 144h; under 2844.39 Torr; optical yield given as %de; Inert atmosphere;
DOI:10.1021/jo2018872

Reference yield:

: 1173701-22-8
(+)-ethyl (5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarboxylate

: 1196491-09-4
ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate

: ethyl (3aR,4S,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: toluene-4-sulfonic acid / acetone / 20 °C / Inert atmosphere

2: copper acetylacetonate / acetonitrile / 5 h / 0 °C / Inert atmosphere

3: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere

4: triphenylphosphine / tetrahydrofuran; water / 12 h

5: triethylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere

6: Rh/Al₂O₃; hydrogen / ethanol / 144 h / 20 °C / 2844.39 Torr / Inert atmosphere

With copper acetylacetonate; sodium azide; Rh/Al₂O₃; hydrogen; ammonium chloride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 4: Staudinger reaction;
DOI:10.1021/jo2018872