tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate
CAS No.:566905-17-7
Molecular Formula:C₃₀H₄₀N₂O₈S
Molecular Weight:588.722
Hs Code.:

tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate

Synonyms:tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate

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Chemical Property of tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate

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Technology Process of tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate

There total 19 articles about tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-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: 43.0%

: 566905-16-6
tert-butyl (3S,5S,10R)-1-(acetyloxy)-10-[5-[3-(acetyloxy)propyl]-3-furyl]-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-carboxylate

: 566905-17-7
tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate

: 566905-40-6
tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1.2h;
DOI:10.1021/ja034464j

Reference yield:

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

: 566905-17-7
tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate

Guidance literature:: Multi-step reaction with 11 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

With dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; lithium borohydride; ethanol; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; 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

: 566905-17-7
tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate

Guidance literature:: Multi-step reaction with 12 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

With dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; lithium borohydride; ethanol; camphor-10-sulfonic acid; potassium acetate; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; 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