(3S,5R,7R)-3-Acetoxy-5-((benzyloxycarbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)cyclohept-1-ene

Base Information

Chemical Name:(3S,5R,7R)-3-Acetoxy-5-((benzyloxycarbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)cyclohept-1-ene
CAS No.:160856-85-9
Molecular Formula:C₂₃H₃₅NO₅Si
Molecular Weight:433.62
Hs Code.:

Synonyms:(3S,5R,7R)-3-Acetoxy-5-((benzyloxycarbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)cyclohept-1-ene

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Chemical Property of (3S,5R,7R)-3-Acetoxy-5-((benzyloxycarbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)cyclohept-1-ene

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Technology Process of (3S,5R,7R)-3-Acetoxy-5-((benzyloxycarbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)cyclohept-1-ene

There total 10 articles about (3S,5R,7R)-3-Acetoxy-5-((benzyloxycarbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)cyclohept-1-ene 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: 99.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 160856-74-6
(1R,4S,6S)-4-Acetoxy-6-((benzyloxycarbonyl)amino)cyclohept-2-en-1-ol

: 160856-85-9
(3S,5R,7R)-3-Acetoxy-5-((benzyloxycarbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)cyclohept-1-ene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; 1.) 0 deg C, 30 min, 2.) r.t., 2 h;
DOI:10.1021/jo00108a025

Reference yield:

: 1121-63-7
cyclohepta-3,5-dien-1-ol

: 160856-85-9
(3S,5R,7R)-3-Acetoxy-5-((benzyloxycarbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)cyclohept-1-ene

Guidance literature:: Multi-step reaction with 8 steps

1: 84 percent / MnO₂, benzoquinone, Pd(OAc)2 / acetic acid / 64 h / 25 °C

2: 100 percent / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

3: 82 percent / NaN₃ / dimethylformamide / 35 h / 50 °C

4: 100 percent / H₂ / Lindlar catalyst / ethanol / 50 h

5: 99 percent / aq. NaHCO₃ / ethyl acetate / 3 h / 25 °C

6: 95 percent / K₂CO₃ / methanol / 2 h

7: 91 percent / various solvent(s) / 86 h / 50 °C / Amano P-30 lipase (crude Pseudomonas cepacia lipase)

8: 99 percent / imidazole / dimethylformamide / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

With 1H-imidazole; manganese(IV) oxide; palladium diacetate; sodium azide; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; p-benzoquinone; Lindlar's catalyst; In methanol; ethanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo00108a025

Reference yield:

: 134780-02-2
meso-(1R,4R,6R)-3,6-Diacetoxy-4-cyclohepten-1-ol

: 160856-85-9
(3S,5R,7R)-3-Acetoxy-5-((benzyloxycarbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)cyclohept-1-ene

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

2: 82 percent / NaN₃ / dimethylformamide / 35 h / 50 °C

3: 100 percent / H₂ / Lindlar catalyst / ethanol / 50 h

4: 99 percent / aq. NaHCO₃ / ethyl acetate / 3 h / 25 °C

5: 95 percent / K₂CO₃ / methanol / 2 h

6: 91 percent / various solvent(s) / 86 h / 50 °C / Amano P-30 lipase (crude Pseudomonas cepacia lipase)

7: 99 percent / imidazole / dimethylformamide / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

With 1H-imidazole; sodium azide; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; Lindlar's catalyst; In methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo00108a025