5,13,15-Hexadecatrien-1-ol, 3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth oxy]-2,4,6,8,10,12-hexamethyl-, (2S,3R,4S,5Z,8S,9R,10R,11S,12S,13Z)-

Base Information

Chemical Name:5,13,15-Hexadecatrien-1-ol, 3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth oxy]-2,4,6,8,10,12-hexamethyl-, (2S,3R,4S,5Z,8S,9R,10R,11S,12S,13Z)-
CAS No.:252342-46-4
Molecular Formula:C42H76O5Si2
Molecular Weight:717.233
Hs Code.:

5,13,15-Hexadecatrien-1-ol,
3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth
oxy]-2,4,6,8,10,12-hexamethyl-,
(2S,3R,4S,5Z,8S,9R,10R,11S,12S,13Z)-

Synonyms:

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Chemical Property of 5,13,15-Hexadecatrien-1-ol, 3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth oxy]-2,4,6,8,10,12-hexamethyl-, (2S,3R,4S,5Z,8S,9R,10R,11S,12S,13Z)-

Chemical Property:

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MSDS Files:: SDS file from LookChem

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Technology Process of 5,13,15-Hexadecatrien-1-ol, 3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth oxy]-2,4,6,8,10,12-hexamethyl-, (2S,3R,4S,5Z,8S,9R,10R,11S,12S,13Z)-

There total 20 articles about 5,13,15-Hexadecatrien-1-ol, 3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)meth oxy]-2,4,6,8,10,12-hexamethyl-, (2S,3R,4S,5Z,8S,9R,10R,11S,12S,13Z)- 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: 95.0%

: 256920-81-7
1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene

: 252342-46-4
(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-trien-1-ol

Guidance literature:: With boron trichloride - methyl sulfide complex; In dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1021/jo050481a

Reference yield:

: 1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-11-trityloxy-undec-6-enyloxymethyl]-4-methoxy-benzene

: (5Z,13E)-(2S,3R,4S,8S,9R,10R,11S,12S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-trien-1-ol

: 252342-46-4
(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-trien-1-ol

Guidance literature:: With methanol; 2-chloro-1,3,2-benzodioxaborole; In dichloromethane; Title compound not separated from byproducts.;
DOI:10.1021/ja0015287

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 252342-46-4
(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-trien-1-ol

Guidance literature:: Multi-step reaction with 10 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

5.1: DMAP; pyridine

6.1: DIBAL-H / 0 °C

7.1: DMP; NaHCO₃

8.2: MeI

9.1: Cl-catecholborane / methanol

With pyridine; dmap; phthalic acid dimethyl ester; 2-chloro-1,3,2-benzodioxaborole; diisobutylaluminium hydride; sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In methanol; diethyl ether; 4.3: Negishi coupling;
DOI:10.1021/ol9910870