(4S,5E,7S,9R,10R)-9,10-epoxy-4-isopropyl-7-<(o-nitrophenyl)selenomethyl>-5-cyclodecen-1-one

Base Information

Chemical Name:(4S,5E,7S,9R,10R)-9,10-epoxy-4-isopropyl-7-<(o-nitrophenyl)selenomethyl>-5-cyclodecen-1-one
CAS No.:132436-32-9
Molecular Formula:C₂₀H₂₅NO₄Se
Molecular Weight:422.383
Hs Code.:

Synonyms:(4S,5E,7S,9R,10R)-9,10-epoxy-4-isopropyl-7-<(o-nitrophenyl)selenomethyl>-5-cyclodecen-1-one

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Chemical Property of (4S,5E,7S,9R,10R)-9,10-epoxy-4-isopropyl-7-<(o-nitrophenyl)selenomethyl>-5-cyclodecen-1-one

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Technology Process of (4S,5E,7S,9R,10R)-9,10-epoxy-4-isopropyl-7-<(o-nitrophenyl)selenomethyl>-5-cyclodecen-1-one

There total 10 articles about (4S,5E,7S,9R,10R)-9,10-epoxy-4-isopropyl-7-<(o-nitrophenyl)selenomethyl>-5-cyclodecen-1-one 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%

: 51694-22-5
ortho-nitrophenyl selenocyanate

: 123536-67-4
(4S,5E,7S,9R,10R)-9,10-epoxy-7-hydroxymethyl-4-isopropyl-5-cyclodecen-1-one

: 132436-32-9
(4S,5E,7S,9R,10R)-9,10-epoxy-4-isopropyl-7-<(o-nitrophenyl)selenomethyl>-5-cyclodecen-1-one

Guidance literature:: With tributylphosphine; In tetrahydrofuran; for 0.833333h; Ambient temperature;
DOI:10.1016/S0040-4020(01)81464-2

Reference yield:

: 123536-65-2
(5S)-5-hydroxymethyl-2-cyclohexen-1-one

: 132436-32-9
(4S,5E,7S,9R,10R)-9,10-epoxy-4-isopropyl-7-<(o-nitrophenyl)selenomethyl>-5-cyclodecen-1-one

Guidance literature:: Multi-step reaction with 8 steps

1: 98.6 percent / PPTS / CH₂Cl₂ / Ambient temperature

2: 1) LDA / 1) -10 deg C to -5 deg C, 20 min, 2) -78 deg C

3: 91 percent / MsCl, NEt₃ / CH₂Cl₂ / 0.25 h

4: 1) PhLi / 1) ether, 30 min, room temperature, 2) ether, -78 deg C, 10 min

5: 86 percent / KH, 18-crown-6 / 1,2-dimethoxy-ethane / 1.17 h / Ambient temperature

6: 1) KH, t-BuOOH / 1) 0 deg C, 15 min, THF, 2) 80 min, -20 deg C, THF

7: PPTS / ethanol / 0.33 h / 50 °C

8: 99 percent / (n-Bu)3P / tetrahydrofuran / 0.83 h / Ambient temperature

With tert.-butylhydroperoxide; 18-crown-6 ether; tributylphosphine; pyridinium p-toluenesulfonate; potassium hydride; methanesulfonyl chloride; phenyllithium; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(01)81464-2

Reference yield:

: 84782-52-5
3-methyl-2-(phenylseleno)butyraldehyde

: 132436-32-9
(4S,5E,7S,9R,10R)-9,10-epoxy-4-isopropyl-7-<(o-nitrophenyl)selenomethyl>-5-cyclodecen-1-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1) LDA / 1) -10 deg C to -5 deg C, 20 min, 2) -78 deg C

2: 91 percent / MsCl, NEt₃ / CH₂Cl₂ / 0.25 h

3: 1) PhLi / 1) ether, 30 min, room temperature, 2) ether, -78 deg C, 10 min

4: 86 percent / KH, 18-crown-6 / 1,2-dimethoxy-ethane / 1.17 h / Ambient temperature

5: 1) KH, t-BuOOH / 1) 0 deg C, 15 min, THF, 2) 80 min, -20 deg C, THF

6: PPTS / ethanol / 0.33 h / 50 °C

7: 99 percent / (n-Bu)3P / tetrahydrofuran / 0.83 h / Ambient temperature

With tert.-butylhydroperoxide; 18-crown-6 ether; tributylphosphine; pyridinium p-toluenesulfonate; potassium hydride; methanesulfonyl chloride; phenyllithium; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(01)81464-2