(6Z,9R,10E,12S,13R)-13-{[tert-butyldiphenylsilyloxy]methyl}-9,12-dihydroxy-1-oxacyclotrideca-6,10-dien-2-one

Base Information

Chemical Name:(6Z,9R,10E,12S,13R)-13-{[tert-butyldiphenylsilyloxy]methyl}-9,12-dihydroxy-1-oxacyclotrideca-6,10-dien-2-one
CAS No.:1330680-37-9
Molecular Formula:C₂₉H₃₈O₅Si
Molecular Weight:494.703
Hs Code.:

Synonyms:(6Z,9R,10E,12S,13R)-13-{[tert-butyldiphenylsilyloxy]methyl}-9,12-dihydroxy-1-oxacyclotrideca-6,10-dien-2-one

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Chemical Property of (6Z,9R,10E,12S,13R)-13-{[tert-butyldiphenylsilyloxy]methyl}-9,12-dihydroxy-1-oxacyclotrideca-6,10-dien-2-one

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Technology Process of (6Z,9R,10E,12S,13R)-13-{[tert-butyldiphenylsilyloxy]methyl}-9,12-dihydroxy-1-oxacyclotrideca-6,10-dien-2-one

There total 12 articles about (6Z,9R,10E,12S,13R)-13-{[tert-butyldiphenylsilyloxy]methyl}-9,12-dihydroxy-1-oxacyclotrideca-6,10-dien-2-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: 76.0%

: 1330680-39-1
(8R,5Z)-((2R,3S)-1-(tert-Butyldiphenylsilyloxy)-3-hydroxypent-4-en-2-yl) 8-hydroxydeca-5,9-dienoate

: 1330680-37-9
(6Z,9R,10E,12S,13R)-13-{[tert-butyldiphenylsilyloxy]methyl}-9,12-dihydroxy-1-oxacyclotrideca-6,10-dien-2-one

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 8.5h; Reflux; Inert atmosphere;
DOI:10.1039/c1ob05335c

Reference yield:

: 1330680-41-5
(2R,3S)-1-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)pent-4-en-2-ol

: 1330680-37-9
(6Z,9R,10E,12S,13R)-13-{[tert-butyldiphenylsilyloxy]methyl}-9,12-dihydroxy-1-oxacyclotrideca-6,10-dien-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5 h / 0 °C / Inert atmosphere

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 0 - 20 °C / Inert atmosphere; aq. phosphate buffer

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8.5 h / Reflux; Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1039/c1ob05335c

Reference yield:

: 1330680-43-7
(R)-tert-butyldimethyl-(7-(oxiran-2-yl)hept-5-ynyloxy)silane

: 1330680-37-9
(6Z,9R,10E,12S,13R)-13-{[tert-butyldiphenylsilyloxy]methyl}-9,12-dihydroxy-1-oxacyclotrideca-6,10-dien-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: quinoline; hydrogen / benzene / 3 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -20 °C

2.2: 2.83 h / -20 - 20 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C / Inert atmosphere

4.1: methanol; toluene-4-sulfonic acid / 1 h / 0 - 20 °C / Inert atmosphere

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

6.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 3 h / 0 - 20 °C / Inert atmosphere

7.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5 h / 0 °C / Inert atmosphere

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 0 - 20 °C / Inert atmosphere; aq. phosphate buffer

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8.5 h / Reflux; Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; quinoline; methanol; dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; hydrogen; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; mineral oil; tert-butyl alcohol; benzene; 6.1: Pinnick oxidation;
DOI:10.1039/c1ob05335c