Toluene-4-sulfonic acid 2-((3aS,6aR)-2-oxo-3-phenylselanyl-hexahydro-furo[3,2-b]pyrrol-4-yl)-ethyl ester

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Chemical Name:Toluene-4-sulfonic acid 2-((3aS,6aR)-2-oxo-3-phenylselanyl-hexahydro-furo[3,2-b]pyrrol-4-yl)-ethyl ester
CAS No.:140192-36-5
Molecular Formula:C₂₁H₂₃NO₅SSe
Molecular Weight:480.443
Hs Code.:

Synonyms:

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Chemical Property of Toluene-4-sulfonic acid 2-((3aS,6aR)-2-oxo-3-phenylselanyl-hexahydro-furo[3,2-b]pyrrol-4-yl)-ethyl ester

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Technology Process of Toluene-4-sulfonic acid 2-((3aS,6aR)-2-oxo-3-phenylselanyl-hexahydro-furo[3,2-b]pyrrol-4-yl)-ethyl ester

There total 11 articles about Toluene-4-sulfonic acid 2-((3aS,6aR)-2-oxo-3-phenylselanyl-hexahydro-furo[3,2-b]pyrrol-4-yl)-ethyl ester 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:

: 109755-67-1
(3R)-3-hydroxy-1-(2-pivaloyloxyethyl)pyrrolidine-2,5-dione

: 140192-36-5,140459-60-5
Toluene-4-sulfonic acid 2-((3aS,6aR)-2-oxo-3-phenylselanyl-hexahydro-furo[3,2-b]pyrrol-4-yl)-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / pyridine / diethyl ether / 0.5 h / Ambient temperature

2: 2) triethylamine / 1) acetonitrile, 50 deg C, 4 h, 2) acetonitrile, 50 deg C, 16 h

3: 99 percent / hydrogen / 5percent rhodium/alumina / ethyl acetate / 3 h / Ambient temperature

4: 602 mg / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) / toluene / 1 h / 105 °C

5: 1) triethyloxonium tetrafluoroborate, 2) NaBH₃CN / 1) dichloromethane, a) 0 deg C, 5 min, b) rt, 1 h, 2) methanol, 0 deg C, 2 h

6: 1) LDA / 1) THF, -78 deg C, 15 min, 2) THF, -78 deg C, 1 h

7: 84 percent / 6 M HCl / methanol / 17 h / 50 °C

8: 1) n-BuLi / 1) THF/hexane, -78 deg C, 5 min, 2) -78 deg C, 1 h

With Lawessons reagent; pyridine; hydrogenchloride; n-butyllithium; hydrogen; triethyloxonium fluoroborate; sodium cyanoborohydride; triethylamine; lithium diisopropyl amide; Rh/Al₂O₃; In methanol; diethyl ether; ethyl acetate; toluene;
DOI:10.1016/S0040-4020(01)89003-7

Reference yield:

: 107319-88-0
(3R)-3-acetoxy-1-(2-acetoxyethyl)pyrrolidine-2,5-dione

: 140192-36-5,140459-60-5
Toluene-4-sulfonic acid 2-((3aS,6aR)-2-oxo-3-phenylselanyl-hexahydro-furo[3,2-b]pyrrol-4-yl)-ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 84 percent / acetyl chloride, ethanol / ethanol / 3 h / 50 °C

2: 66 percent / pyridine; diethyl ether / 1 h / -30 °C

3: 94 percent / pyridine / diethyl ether / 0.5 h / Ambient temperature

4: 2) triethylamine / 1) acetonitrile, 50 deg C, 4 h, 2) acetonitrile, 50 deg C, 16 h

5: 99 percent / hydrogen / 5percent rhodium/alumina / ethyl acetate / 3 h / Ambient temperature

6: 602 mg / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) / toluene / 1 h / 105 °C

7: 1) triethyloxonium tetrafluoroborate, 2) NaBH₃CN / 1) dichloromethane, a) 0 deg C, 5 min, b) rt, 1 h, 2) methanol, 0 deg C, 2 h

8: 1) LDA / 1) THF, -78 deg C, 15 min, 2) THF, -78 deg C, 1 h

9: 84 percent / 6 M HCl / methanol / 17 h / 50 °C

10: 1) n-BuLi / 1) THF/hexane, -78 deg C, 5 min, 2) -78 deg C, 1 h

With Lawessons reagent; pyridine; hydrogenchloride; n-butyllithium; ethanol; hydrogen; triethyloxonium fluoroborate; sodium cyanoborohydride; triethylamine; acetyl chloride; lithium diisopropyl amide; Rh/Al₂O₃; In pyridine; methanol; diethyl ether; ethanol; ethyl acetate; toluene;
DOI:10.1016/S0040-4020(01)89003-7

Reference yield:

: 107319-90-4
(1R)-6-(2-pivaloyloxyethyl)-2-oxa-6-azabicyclo<3.3.0>oct-4-ene-3,7-dione

: 140192-36-5,140459-60-5
Toluene-4-sulfonic acid 2-((3aS,6aR)-2-oxo-3-phenylselanyl-hexahydro-furo[3,2-b]pyrrol-4-yl)-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / hydrogen / 5percent rhodium/alumina / ethyl acetate / 3 h / Ambient temperature

2: 602 mg / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) / toluene / 1 h / 105 °C

3: 1) triethyloxonium tetrafluoroborate, 2) NaBH₃CN / 1) dichloromethane, a) 0 deg C, 5 min, b) rt, 1 h, 2) methanol, 0 deg C, 2 h

4: 1) LDA / 1) THF, -78 deg C, 15 min, 2) THF, -78 deg C, 1 h

5: 84 percent / 6 M HCl / methanol / 17 h / 50 °C

6: 1) n-BuLi / 1) THF/hexane, -78 deg C, 5 min, 2) -78 deg C, 1 h

With Lawessons reagent; hydrogenchloride; n-butyllithium; hydrogen; triethyloxonium fluoroborate; sodium cyanoborohydride; lithium diisopropyl amide; Rh/Al₂O₃; In methanol; ethyl acetate; toluene;
DOI:10.1016/S0040-4020(01)89003-7