(1S,5S,7S)-5-((Benzyloxycarbonyl)amino)-9,9-dimethyl-8,10-dioxabicyclo<5.3.0>cyclodec-2-ene

Base Information

Chemical Name:(1S,5S,7S)-5-((Benzyloxycarbonyl)amino)-9,9-dimethyl-8,10-dioxabicyclo<5.3.0>cyclodec-2-ene
CAS No.:160856-82-6
Molecular Formula:C₁₈H₂₃NO₄
Molecular Weight:317.385
Hs Code.:

Synonyms:(1S,5S,7S)-5-((Benzyloxycarbonyl)amino)-9,9-dimethyl-8,10-dioxabicyclo<5.3.0>cyclodec-2-ene

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Chemical Property of (1S,5S,7S)-5-((Benzyloxycarbonyl)amino)-9,9-dimethyl-8,10-dioxabicyclo<5.3.0>cyclodec-2-ene

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Technology Process of (1S,5S,7S)-5-((Benzyloxycarbonyl)amino)-9,9-dimethyl-8,10-dioxabicyclo<5.3.0>cyclodec-2-ene

There total 13 articles about (1S,5S,7S)-5-((Benzyloxycarbonyl)amino)-9,9-dimethyl-8,10-dioxabicyclo<5.3.0>cyclodec-2-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: 95.0%

: 77-76-9
2,2-dimethoxy-propane

: 160856-81-5
(1S,2S,6S)-6-((Benzyloxycarbonyl)amino)cyclohept-3-ene-1,2-diol

: 160856-82-6
(1S,5S,7S)-5-((Benzyloxycarbonyl)amino)-9,9-dimethyl-8,10-dioxabicyclo<5.3.0>cyclodec-2-ene

Guidance literature:: With toluene-4-sulfonic acid; In acetone; for 0.25h; Ambient temperature;
DOI:10.1021/jo00108a025

Reference yield:

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

: 160856-82-6
(1S,5S,7S)-5-((Benzyloxycarbonyl)amino)-9,9-dimethyl-8,10-dioxabicyclo<5.3.0>cyclodec-2-ene

Guidance literature:: Multi-step reaction with 11 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: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

9: NaBH₄ / ethanol / 3 h / 0 °C

10: 1.) 30percent H₂O₂, 2.) K₂CO₃ / 1.) THF, CH₂Cl₂,-78 to 0 deg C, 3 h; 0 deg C, to r.t., 3 h, 2.) MeOH, 25 min

11: 95 percent / p-TSA / acetone / 0.25 h / Ambient temperature

With manganese(IV) oxide; palladium diacetate; sodium tetrahydroborate; sodium azide; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; p-benzoquinone; Lindlar's catalyst; In methanol; ethanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00108a025

Reference yield:

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

: 160856-82-6
(1S,5S,7S)-5-((Benzyloxycarbonyl)amino)-9,9-dimethyl-8,10-dioxabicyclo<5.3.0>cyclodec-2-ene

Guidance literature:: Multi-step reaction with 10 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: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

8: NaBH₄ / ethanol / 3 h / 0 °C

9: 1.) 30percent H₂O₂, 2.) K₂CO₃ / 1.) THF, CH₂Cl₂,-78 to 0 deg C, 3 h; 0 deg C, to r.t., 3 h, 2.) MeOH, 25 min

10: 95 percent / p-TSA / acetone / 0.25 h / Ambient temperature

With sodium tetrahydroborate; sodium azide; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; Lindlar's catalyst; In methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00108a025