(2S,11R,12S)-1-(tert-butyldiphenylsilyloxy)-2-(p-methoxybenzyloxy)-11,12-methylene-9,13-octadiene

Base Information

Chemical Name:(2S,11R,12S)-1-(tert-butyldiphenylsilyloxy)-2-(p-methoxybenzyloxy)-11,12-methylene-9,13-octadiene
CAS No.:221677-52-7
Molecular Formula:C₄₃H₆₀O₃Si
Molecular Weight:653.033
Hs Code.:

Synonyms:(2S,11R,12S)-1-(tert-butyldiphenylsilyloxy)-2-(p-methoxybenzyloxy)-11,12-methylene-9,13-octadiene

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Chemical Property of (2S,11R,12S)-1-(tert-butyldiphenylsilyloxy)-2-(p-methoxybenzyloxy)-11,12-methylene-9,13-octadiene

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Technology Process of (2S,11R,12S)-1-(tert-butyldiphenylsilyloxy)-2-(p-methoxybenzyloxy)-11,12-methylene-9,13-octadiene

There total 12 articles about (2S,11R,12S)-1-(tert-butyldiphenylsilyloxy)-2-(p-methoxybenzyloxy)-11,12-methylene-9,13-octadiene 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:

: 221677-68-5
(2S,3R,4R,13S)-14-(tert-butyldiphenylsilyloxy)-13-(p-methoxybenzyloxy)-3,4-methylene-5-tetradecen-1,2-diol

: 221677-52-7
(2S,11R,12S)-1-(tert-butyldiphenylsilyloxy)-2-(p-methoxybenzyloxy)-11,12-methylene-9,13-octadiene

Guidance literature:: Multi-step reaction with 2 steps

1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

2: 1.) n-BuLi / 1.) THF, hexane, room temperature, 30 min, 2.) THF, -78 deg C -> room temperature, 30 min

With sodium periodate; n-butyllithium; In tetrahydrofuran; water;
DOI:10.1016/S0040-4020(99)00248-3

Reference yield:

: 103708-37-8
(2S,4S)-4-hydroxymethyl-2-(p-methoxymethyl)-1,3-dioxane

: 221677-52-7
(2S,11R,12S)-1-(tert-butyldiphenylsilyloxy)-2-(p-methoxybenzyloxy)-11,12-methylene-9,13-octadiene

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / imidazole / dimethylformamide

2: 82 percent / DIBAL-H / toluene

3: 97 percent / pyridine / CH₂Cl₂

4: CuI / tetrahydrofuran

5: 1.) PPTS; 2.) CBr₄, Ph₃P / 1.) EtOH; 2.) CH₂Cl₂

6: acetonitrile / Heating

7: 82 percent / n-BuLi / tetrahydrofuran

8: 72 percent / PPTS / ethanol

9: NaIO₄ / tetrahydrofuran; H₂O

10: n-BuLi / tetrahydrofuran

With pyridine; 1H-imidazole; sodium periodate; copper(l) iodide; n-butyllithium; carbon tetrabromide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4039(98)02494-0

Reference yield:

: 153861-49-5
(1R,2S,4'S)-1-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-2-(hydroxymethyl)cyclopropane

: 221677-52-7
(2S,11R,12S)-1-(tert-butyldiphenylsilyloxy)-2-(p-methoxybenzyloxy)-11,12-methylene-9,13-octadiene

Guidance literature:: Multi-step reaction with 5 steps

1: Swern reagent

2: 82 percent / n-BuLi / tetrahydrofuran

3: 72 percent / PPTS / ethanol

4: NaIO₄ / tetrahydrofuran; H₂O

5: n-BuLi / tetrahydrofuran

With sodium periodate; n-butyllithium; swern reagent; pyridinium p-toluenesulfonate; In tetrahydrofuran; ethanol; water;
DOI:10.1016/S0040-4039(98)02494-0