(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol

Base Information

Chemical Name:(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol
CAS No.:252342-52-2
Molecular Formula:C₃₉H₇₂O₆Si₂
Molecular Weight:693.168
Hs Code.:

(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol

Synonyms:(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol

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Chemical Property of (Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol

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Technology Process of (Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol

There total 19 articles about (Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol 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: 98.0%

: 252342-44-2
(2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-bis(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-1,3,5,7,9-pentamethyldec-5-enyl]-2-(4-methoxyphenyl)-5-methyl-[1,3]dioxane

: 252342-52-2
(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 3h;
DOI:10.1021/ja0015287

Reference yield:

: 132969-62-1
(2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone

: 252342-52-2
(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: Me₃Al / -78 °C

2.1: Lut_.

3.1: DIBAL-H / -78 °C

4.1: ZnCl₂ / diethyl ether

4.2: t-BuLi / diethyl ether / -78 - 20 °C

4.3: 66 percent / Pd(PPh₃)4 / diethyl ether

5.1: DDQ

With trimethylaluminum; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In diethyl ether; 5.3: Negishi coupling;
DOI:10.1021/ol9910870

Reference yield:

: 252342-49-7
(2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide

: 252342-52-2
(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,6,8-tetramethyl-undec-5-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: Lut_.

2.1: DIBAL-H / -78 °C

3.1: ZnCl₂ / diethyl ether

3.2: t-BuLi / diethyl ether / -78 - 20 °C

3.3: 66 percent / Pd(PPh₃)4 / diethyl ether

4.1: DDQ

With diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In diethyl ether; 4.3: Negishi coupling;
DOI:10.1021/ol9910870