(4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-ol

Base Information

Chemical Name:(4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-ol
CAS No.:511256-77-2
Molecular Formula:C₃₅H₅₄O₅Si₂
Molecular Weight:610.982
Hs Code.:

(4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-ol

Synonyms:(4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-ol

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Chemical Property of (4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-ol

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Technology Process of (4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-ol

There total 10 articles about (4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-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: 90.0%

: 33324-92-4
(2-methylallyl)magnesium bromide

: 511256-76-1
(4aR,8R,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-silanaphthalene

: 511256-77-2
(4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-ol

Guidance literature:: (4aR,8R,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-silanaphthalene; With 3,3-dimethyldioxirane; In dichloromethane; at -65 ℃; for 0.5h;

(2-methylallyl)magnesium bromide; In dichloromethane; at -65 ℃; for 0.25h;
DOI:10.1021/ol034100w

Reference yield:

: 511256-75-0
(4aR,8R,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-silanaphthalene

: 511256-77-2
(4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / t-BuLi

2: dimethyldioxirane

3: CuI / tetrahydrofuran

With copper(l) iodide; tert.-butyl lithium; 3,3-dimethyldioxirane; In tetrahydrofuran;
DOI:10.1002/chem.200500993

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 511256-77-2
(4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-8-(tert-butyldiphenylsilanyloxy)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / 0 °C

2.2: 95 percent / tetrahydrofuran; pentane / -70 - 20 °C

3.1: dimethyl dioxirane / CH₂Cl₂ / 0.5 h / -65 °C

3.2: 90 percent / CH₂Cl₂ / 0.25 h / -65 °C

With 1H-imidazole; tert.-butyl lithium; 3,3-dimethyldioxirane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol034100w