tert-butyl (3S,5S,10R)-10-(5-[3-[(tert-butoxycarbonyl)oxy]propyl]-3-furyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-carboxylate

Base Information

Chemical Name:tert-butyl (3S,5S,10R)-10-(5-[3-[(tert-butoxycarbonyl)oxy]propyl]-3-furyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-carboxylate
CAS No.:566905-15-5
Molecular Formula:C₃₈H₅₄N₂O₁₁S
Molecular Weight:746.92
Hs Code.:

tert-butyl (3S,5S,10R)-10-(5-[3-[(tert-butoxycarbonyl)oxy]propyl]-3-furyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-carboxylate

Synonyms:tert-butyl (3S,5S,10R)-10-(5-[3-[(tert-butoxycarbonyl)oxy]propyl]-3-furyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-carboxylate

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Chemical Property of tert-butyl (3S,5S,10R)-10-(5-[3-[(tert-butoxycarbonyl)oxy]propyl]-3-furyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-carboxylate

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Technology Process of tert-butyl (3S,5S,10R)-10-(5-[3-[(tert-butoxycarbonyl)oxy]propyl]-3-furyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-carboxylate

There total 13 articles about tert-butyl (3S,5S,10R)-10-(5-[3-[(tert-butoxycarbonyl)oxy]propyl]-3-furyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-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: 68.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 566905-37-1
(3S,5S,10R)-10-[5-(3-hydroxypropyl)-3-furyl]-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decan-1-one

: 566905-15-5
tert-butyl (3S,5S,10R)-10-(5-[3-[(tert-butoxycarbonyl)oxy]propyl]-3-furyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-carboxylate

: 566905-38-2
bis[3-[4-((3S,5S,10R)-2-(tert-butoxycarbonyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]dec-10-yl)-2-furyl]propyl] carbonate

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 11h;
DOI:10.1021/ja034464j

Reference yield:

: 21921-76-6
4-bromo-2-furancarbaldehyde

: 566905-15-5
tert-butyl (3S,5S,10R)-10-(5-[3-[(tert-butoxycarbonyl)oxy]propyl]-3-furyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: sodium t-butoxide / tetrahydrofuran / 1.5 h / 0 - 20 °C

1.2: 96 percent / tetrahydrofuran / 1.5 h / 4 - 20 °C

2.1: 92 percent / NiCl₂; NaBH₄ / ethanol / 1 h / 0 °C

3.1: 82 percent / potasium acetate; PdCl₂(dppf) / dimethylsulfoxide / 5 h / 82 °C

4.1: 95 percent / K₃PO₄; PdCl₂(dppf) / dimethylformamide / 3 h / 80 °C

5.1: 92 percent / Pd/C / methanol / 1.5 h / 20 °C

6.1: 72 percent / PPTS; EtOH / methanol / 3 h / 50 °C

7.1: 96 percent / CSA / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 94 percent / LiBH₄ / methanol; tetrahydrofuran / 19 h / 3 - 20 °C

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

10.1: 5.71 g / aq. NaHCO₃ / ethyl acetate / 1 h / 20 °C

11.1: 68 percent / DMAP; Et₃N / tetrahydrofuran / 11 h / 20 °C

With dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; potassium phosphate; lithium borohydride; ethanol; camphor-10-sulfonic acid; potassium acetate; pyridinium p-toluenesulfonate; lithium; sodium hydrogencarbonate; triethylamine; nickel dichloride; sodium t-butanolate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ammonia; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 4.1: Suzuki-Miyaura coupling;
DOI:10.1021/ja034464j

Reference yield:

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

: 566905-15-5
tert-butyl (3S,5S,10R)-10-(5-[3-[(tert-butoxycarbonyl)oxy]propyl]-3-furyl)-1-oxo-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diazaspiro[4.5]decane-2-carboxylate

Guidance literature:: Multi-step reaction with 9 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

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; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ammonia; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 2: Suzuki-Miyaura coupling;
DOI:10.1021/ja034464j