3-[(2S,3aS,7aS,10bS)-1-(5-hexenoyl)-5-(phenylsulfonyl)-2-vinyl-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridin-9-yl]propyl acetate

Base Information

Chemical Name:3-[(2S,3aS,7aS,10bS)-1-(5-hexenoyl)-5-(phenylsulfonyl)-2-vinyl-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridin-9-yl]propyl acetate
CAS No.:566905-19-9
Molecular Formula:C₃₁H₃₈N₂O₆S
Molecular Weight:566.719
Hs Code.:

3-[(2S,3aS,7aS,10bS)-1-(5-hexenoyl)-5-(phenylsulfonyl)-2-vinyl-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridin-9-yl]propyl acetate

Synonyms:3-[(2S,3aS,7aS,10bS)-1-(5-hexenoyl)-5-(phenylsulfonyl)-2-vinyl-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridin-9-yl]propyl acetate

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Chemical Property of 3-[(2S,3aS,7aS,10bS)-1-(5-hexenoyl)-5-(phenylsulfonyl)-2-vinyl-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridin-9-yl]propyl acetate

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Technology Process of 3-[(2S,3aS,7aS,10bS)-1-(5-hexenoyl)-5-(phenylsulfonyl)-2-vinyl-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridin-9-yl]propyl acetate

There total 22 articles about 3-[(2S,3aS,7aS,10bS)-1-(5-hexenoyl)-5-(phenylsulfonyl)-2-vinyl-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridin-9-yl]propyl acetate 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:

: 390748-07-9
ethyl 3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-2-furyl]propanoate

: 566905-19-9
3-[(2S,3aS,7aS,10bS)-1-(5-hexenoyl)-5-(phenylsulfonyl)-2-vinyl-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridin-9-yl]propyl acetate

Guidance literature:: Multi-step reaction with 15 steps

1: 95 percent / K₃PO₄; PdCl₂(dppf) / dimethylformamide / 3 h / 80 °C

2: 92 percent / Pd/C / methanol / 1.5 h / 20 °C

3: 72 percent / PPTS; EtOH / methanol / 3 h / 50 °C

4: 96 percent / CSA / CH₂Cl₂ / 1.5 h / 20 °C

5: 94 percent / LiBH₄ / methanol; tetrahydrofuran / 19 h / 3 - 20 °C

6: lithium / tetrahydrofuran; liquid ammonia / 0.5 h / -78 °C

7: 5.71 g / aq. NaHCO₃ / ethyl acetate / 1 h / 20 °C

8: 68 percent / DMAP; Et₃N / tetrahydrofuran / 11 h / 20 °C

9: DIBAL-H / toluene; CH₂Cl₂ / 2 h / -78 - 20 °C

10: 7.57 g / pyridine / 12 h / 20 °C

11: 37 percent / p-TsOH monohydrate / CH₂Cl₂ / 1.2 h / 20 °C

12: tri-n-butylphosphine / tetrahydrofuran / 16 h / 20 °C

13: 3.09 g / aq. K₂HPO₄; mCPBA / CH₂Cl₂ / 0.5 h / 0 °C

14: TFA / CH₂Cl₂ / 0.5 h / 20 °C

15: 1.76 g / 1-hydroxybenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide*HCl / tetrahydrofuran / 3 h / 20 °C

With dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; dipotassium hydrogenphosphate; lithium borohydride; ethanol; tributylphosphine; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; ammonia; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Suzuki-Miyaura coupling;
DOI:10.1021/ja034464j

Reference yield:

: 390748-06-8
ethyl 3-(4-bromo-2-furyl)propanoate

: 566905-19-9
3-[(2S,3aS,7aS,10bS)-1-(5-hexenoyl)-5-(phenylsulfonyl)-2-vinyl-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridin-9-yl]propyl acetate

Guidance literature:: Multi-step reaction with 16 steps

1: 82 percent / potasium acetate; PdCl₂(dppf) / dimethylsulfoxide / 5 h / 82 °C

2: 95 percent / K₃PO₄; PdCl₂(dppf) / dimethylformamide / 3 h / 80 °C

3: 92 percent / Pd/C / methanol / 1.5 h / 20 °C

4: 72 percent / PPTS; EtOH / methanol / 3 h / 50 °C

5: 96 percent / CSA / CH₂Cl₂ / 1.5 h / 20 °C

6: 94 percent / LiBH₄ / methanol; tetrahydrofuran / 19 h / 3 - 20 °C

7: lithium / tetrahydrofuran; liquid ammonia / 0.5 h / -78 °C

8: 5.71 g / aq. NaHCO₃ / ethyl acetate / 1 h / 20 °C

9: 68 percent / DMAP; Et₃N / tetrahydrofuran / 11 h / 20 °C

10: DIBAL-H / toluene; CH₂Cl₂ / 2 h / -78 - 20 °C

11: 7.57 g / pyridine / 12 h / 20 °C

12: 37 percent / p-TsOH monohydrate / CH₂Cl₂ / 1.2 h / 20 °C

13: tri-n-butylphosphine / tetrahydrofuran / 16 h / 20 °C

14: 3.09 g / aq. K₂HPO₄; mCPBA / CH₂Cl₂ / 0.5 h / 0 °C

15: TFA / CH₂Cl₂ / 0.5 h / 20 °C

16: 1.76 g / 1-hydroxybenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide*HCl / tetrahydrofuran / 3 h / 20 °C

With dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; dipotassium hydrogenphosphate; lithium borohydride; ethanol; tributylphosphine; camphor-10-sulfonic acid; potassium acetate; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; ammonia; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; 2: Suzuki-Miyaura coupling;
DOI:10.1021/ja034464j

Reference yield:

: 566905-10-0
(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-7-(phenylsulfonyl)-2,7-diazaspiro[4.5]decane-1,10-dione

: 566905-19-9
3-[(2S,3aS,7aS,10bS)-1-(5-hexenoyl)-5-(phenylsulfonyl)-2-vinyl-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridin-9-yl]propyl acetate

Guidance literature:: Multi-step reaction with 17 steps

1.1: 90 percent / CSA / CH₂Cl₂ / 1.5 h / 20 °C

2.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -78 °C

2.2: 92 percent / tetrahydrofuran / 13 h / 20 °C

3.1: 95 percent / K₃PO₄; PdCl₂(dppf) / dimethylformamide / 3 h / 80 °C

4.1: 92 percent / Pd/C / methanol / 1.5 h / 20 °C

5.1: 72 percent / PPTS; EtOH / methanol / 3 h / 50 °C

6.1: 96 percent / CSA / CH₂Cl₂ / 1.5 h / 20 °C

7.1: 94 percent / LiBH₄ / methanol; tetrahydrofuran / 19 h / 3 - 20 °C

8.1: lithium / tetrahydrofuran; liquid ammonia / 0.5 h / -78 °C

9.1: 5.71 g / aq. NaHCO₃ / ethyl acetate / 1 h / 20 °C

10.1: 68 percent / DMAP; Et₃N / tetrahydrofuran / 11 h / 20 °C

11.1: DIBAL-H / toluene; CH₂Cl₂ / 2 h / -78 - 20 °C

12.1: 7.57 g / pyridine / 12 h / 20 °C

13.1: 37 percent / p-TsOH monohydrate / CH₂Cl₂ / 1.2 h / 20 °C

14.1: tri-n-butylphosphine / tetrahydrofuran / 16 h / 20 °C

15.1: 3.09 g / aq. K₂HPO₄; mCPBA / CH₂Cl₂ / 0.5 h / 0 °C

16.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

17.1: 1.76 g / 1-hydroxybenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide*HCl / tetrahydrofuran / 3 h / 20 °C

With dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; dipotassium hydrogenphosphate; lithium borohydride; ethanol; tributylphosphine; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; ammonia; ethyl acetate; N,N-dimethyl-formamide; toluene; 3.1: Suzuki-Miyaura coupling;
DOI:10.1021/ja034464j