(1R,5S,11R,14S,9Z)-14-(benzyloxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

Base Information

Chemical Name:(1R,5S,11R,14S,9Z)-14-(benzyloxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one
CAS No.:1211843-98-9
Molecular Formula:C₂₁H₂₈O₄
Molecular Weight:344.451
Hs Code.:

Synonyms:(1R,5S,11R,14S,9Z)-14-(benzyloxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

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Chemical Property of (1R,5S,11R,14S,9Z)-14-(benzyloxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

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Technology Process of (1R,5S,11R,14S,9Z)-14-(benzyloxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

There total 21 articles about (1R,5S,11R,14S,9Z)-14-(benzyloxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-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%

: (2S)-hept-6-en-2-yl 2-[(2R,3S,6R)-3-(benzyloxy)-6-(prop-1-enyl)tetrahydro-2H-pyran-2-yl]acetate

: 1211843-98-9
(1R,5S,11R,14S,9Z)-14-(benzyloxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; for 7h; stereoselective reaction; Reflux; Inert atmosphere;
DOI:10.1021/jo9027038

Reference yield: 28.0%

: 2-{(2R,3S,6R)-3-(benzyloxy)-6-[(6S)-hydroxyhept-1-enyl]tetrahydropyran-2-yl}acetic acid

: 1211843-98-9
(1R,5S,11R,14S,9Z)-14-(benzyloxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

Guidance literature:: 2-{(2R,3S,6R)-3-(benzyloxy)-6-[(6S)-hydroxyhept-1-enyl]tetrahydropyran-2-yl}acetic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

With dmap; In tetrahydrofuran; toluene; at 20 - 50 ℃;
DOI:10.1021/jo9027038

Reference yield:

: 1372785-70-0
(3R,4S)-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)oct-7-en-3-ol

: 1211843-98-9
(1R,5S,11R,14S,9Z)-14-(benzyloxy)-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

1.2: 5 h / 0 - 20 °C

2.1: ozone / dichloromethane / 0.25 h / -78 °C

2.2: -78 °C

3.1: benzene / 2 h / Reflux

4.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / 0 °C

4.2: 1 h / 20 °C

5.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C

6.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; Cumene hydroperoxide / dichloromethane / 6 h / -20 °C / Molecular sieve

6.2: 3 h / -20 - 20 °C

7.1: sodium periodate / water; acetone / 0.5 h / 20 °C

8.1: tetrahydrofuran / 1 h / 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

10.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 0 °C

11.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

11.2: 5 h / 0 - 20 °C / Inert atmosphere

12.1: Grubbs catalyst first generation / dichloromethane / 4 h / Reflux; Inert atmosphere

With Grubbs catalyst first generation; titanium(IV) isopropylate; dmap; sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; L-(+)-diisopropyl tartrate; [bis(acetoxy)iodo]benzene; Cumene hydroperoxide; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; acetone; benzene; 3.1: Wittig reaction / 6.1: Sharpless asymmetric epoxidation / 8.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.02.009