(E)-(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-9,19-dien-3-yn-5-one

Base Information

Chemical Name:(E)-(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-9,19-dien-3-yn-5-one
CAS No.:911834-88-3
Molecular Formula:C₃₂H₄₆O₆
Molecular Weight:526.714
Hs Code.:

(E)-(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-9,19-dien-3-yn-5-one

Synonyms:(E)-(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-9,19-dien-3-yn-5-one

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Chemical Property of (E)-(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-9,19-dien-3-yn-5-one

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Technology Process of (E)-(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-9,19-dien-3-yn-5-one

There total 19 articles about (E)-(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-9,19-dien-3-yn-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: 68.0%

: 911834-80-5
(E)-(1R,7S,11S,15S,17R)-7-((S)-1-Hydroxy-allyl)-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-9,19-dien-3-yn-5-one

: 695-12-5,25498-06-0
vinylcyclohexane

: 911834-88-3
(E)-(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-9,19-dien-3-yn-5-one

Guidance literature:: With Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/ol061619u

Reference yield:

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

: 911834-88-3
(E)-(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-9,19-dien-3-yn-5-one

Guidance literature:: Multi-step reaction with 12 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

With hydrogenchloride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; ammonium cerium(IV) nitrate; D-tartaric acid derivative; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; chloroform; 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

: 911834-88-3
(E)-(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-9,19-dien-3-yn-5-one

Guidance literature:: Multi-step reaction with 10 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

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