(2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3,5-diol

Base Information

Chemical Name:(2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3,5-diol
CAS No.:346708-33-6
Molecular Formula:C₂₉H₅₀O₅Si
Molecular Weight:506.798
Hs Code.:

Synonyms:(2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3,5-diol

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Chemical Property of (2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3,5-diol

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Technology Process of (2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3,5-diol

There total 12 articles about (2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3,5-diol 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%

: 915234-74-1
(2R,4R,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-5-hydroxy-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3-one

: 346708-33-6
(2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3,5-diol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; Inert atmosphere;
DOI:10.1002/chem.200701529

Reference yield: 42.0%

: 346708-32-5
(1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane

: 346708-33-6
(2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3,5-diol

Guidance literature:: With zinc(II) nitrate; In acetonitrile; at 50 ℃;
DOI:10.1016/S0040-4039(01)00401-4

Reference yield:

: 160238-46-0
(2R)-3-(4-methoxybenzyloxy)-2-methyl-1-propanal

: 346708-33-6
(2R,3S,4S,5S,6E,8S,9Z)-4-(tert-butyldimethylsilyloxymethyl)-1-(p-methoxybenzyloxy)-2,6,8-trimethylundeca-6,9-diene-3,5-diol

Guidance literature:: Multi-step reaction with 11 steps

1.1: LDA / tetrahydrofuran / -78 °C

2.1: DIBAL-H / diethyl ether / 0 °C

3.1: pyridine / 0 °C

4.1: 95 percent / CH₂Cl₂ / 0 °C

5.1: (c-hex)2BCl; Et₃N / diethyl ether / -78 - 0 °C

5.2: diethyl ether / -78 - -20 °C

6.1: Et₂BOMe; NaBH₄ / methanol; tetrahydrofuran / -78 °C

7.1: 100 percent / PPTS / CH₂Cl₂ / 0 - 20 °C

8.1: 72 percent / 10 percent NaOH / methanol / 8 h / Heating

9.1: 85 percent / pyridine / CH₂Cl₂ / 0 °C

10.1: n-BuLi / tetrahydrofuran / -78 - 0 °C

10.2: 93 percent / tetrahydrofuran / -78 - 20 °C

11.1: 42 percent / Zn(NO₃)2*6H₂O / acetonitrile / 50 °C

With pyridine; sodium hydroxide; zinc(II) nitrate; sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; dicyclohexylboron chloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 4.1: Dess-Martin periodinane oxidation / 5.1: Paterson reaction / 9.1: Dess-Martin periodinane oxidation / 10.2: Wittig reaction;
DOI:10.1016/S0040-4039(01)00401-4