(3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-hydroxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Base Information

Chemical Name:(3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-hydroxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one
CAS No.:911834-91-8
Molecular Formula:C₃₀H₄₄O₅
Molecular Weight:484.676
Hs Code.:

Synonyms:(3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-hydroxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

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Chemical Property of (3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-hydroxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

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Technology Process of (3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-hydroxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

There total 21 articles about (3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-hydroxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-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: 73.0%

: 911834-96-3
(3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

: 911834-91-8
(3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-hydroxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Guidance literature:: With dimethylboron bromide; triethylamine; In dichloromethane; 1,2-dichloro-ethane; at -78 - 20 ℃; for 4h;
DOI:10.1021/ol061619u

Reference yield:

: 1058706-86-7
(S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane

: 911834-91-8
(3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-hydroxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: NaHMDS / tetrahydrofuran / 1.5 h / -30 - -20 °C

1.2: 843 mg / tetrahydrofuran / 5 h / -20 - 20 °C

2.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C

3.1: Et₃N / CH₂Cl₂ / 0.17 h / -78 °C

3.2: 1.01 g / CH₂Cl₂ / 1.25 h / -78 - 20 °C

4.1: 99 percent / cerium(IV) ammonium nitrate / propan-2-ol / 24 h / 20 °C

5.1: 84 percent / K₂CO₃; Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

6.1: 87 percent / DBU / CHCl₃ / 3.5 h / 20 °C

7.1: D-tartaric acid derivative / various solvent(s) / 56 h / -78 °C

8.1: 99.5 percent / diisopropylethylamine / CH₂Cl₂ / 20 h / 20 °C

9.1: 90 percent / TBAF / tetrahydrofuran / 3 h / 0 - 20 °C

10.1: n-BuLi / tetrahydrofuran / 0.12 h / -78 °C

10.2: 94 percent / tetrahydrofuran / 0.17 h / -78 °C

11.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / benzene / 0.53 h / 20 °C

11.2: 43 percent / DMAP / benzene / 1 h / 20 °C

12.1: 68 percent / Cl₂(PCy₃)(1,3-dimesitylimidazolidin-2-yl)Ru=CHPH / CH₂Cl₂ / 24 h / 20 °C

13.1: 65 percent / 1-hexene; quinoline; H₂ / Lindlar catalyst / ethyl acetate / 2.5 h / 20 °C

14.1: 73 percent / Et₃N; dimethylbromoborane / CH₂Cl₂; 1,2-dichloro-ethane / 4 h / -78 - 20 °C

With quinoline; hydrogenchloride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; 1-hexene; ammonium cerium(IV) nitrate; dimethylboron bromide; D-tartaric acid derivative; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; 1,2-dichloro-ethane; isopropyl alcohol; benzene; 1.2: Wiitig olefination;
DOI:10.1021/ol061619u

Reference yield:

: (Z)-(3S,4S)-8-(tert-Butyl-dimethyl-silanyloxy)-octa-1,5-diene-3,4-diol

: 911834-91-8
(3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-hydroxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: Et₃N / CH₂Cl₂ / 0.17 h / -78 °C

1.2: 1.01 g / CH₂Cl₂ / 1.25 h / -78 - 20 °C

2.1: 99 percent / cerium(IV) ammonium nitrate / propan-2-ol / 24 h / 20 °C

3.1: 84 percent / K₂CO₃; Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

4.1: 87 percent / DBU / CHCl₃ / 3.5 h / 20 °C

5.1: D-tartaric acid derivative / various solvent(s) / 56 h / -78 °C

6.1: 99.5 percent / diisopropylethylamine / CH₂Cl₂ / 20 h / 20 °C

7.1: 90 percent / TBAF / tetrahydrofuran / 3 h / 0 - 20 °C

8.1: n-BuLi / tetrahydrofuran / 0.12 h / -78 °C

8.2: 94 percent / tetrahydrofuran / 0.17 h / -78 °C

9.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / benzene / 0.53 h / 20 °C

9.2: 43 percent / DMAP / benzene / 1 h / 20 °C

10.1: 68 percent / Cl₂(PCy₃)(1,3-dimesitylimidazolidin-2-yl)Ru=CHPH / CH₂Cl₂ / 24 h / 20 °C

11.1: 65 percent / 1-hexene; quinoline; H₂ / Lindlar catalyst / ethyl acetate / 2.5 h / 20 °C

12.1: 73 percent / Et₃N; dimethylbromoborane / CH₂Cl₂; 1,2-dichloro-ethane / 4 h / -78 - 20 °C

With quinoline; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; 1-hexene; ammonium cerium(IV) nitrate; dimethylboron bromide; D-tartaric acid derivative; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; 1,2-dichloro-ethane; isopropyl alcohol; benzene;
DOI:10.1021/ol061619u