(4a′S,5′S,8a′S)-5′-[2-(tert-butyldimethylsiloxy)-3-methoxybenzyl]-5′,8a′-dimethylhexahydro-2′Hspiro{[1,3]dioxolane-2,1′-naphthalen}-6′(7′H)-one

Base Information

Chemical Name:(4a′S,5′S,8a′S)-5′-[2-(tert-butyldimethylsiloxy)-3-methoxybenzyl]-5′,8a′-dimethylhexahydro-2′Hspiro{[1,3]dioxolane-2,1′-naphthalen}-6′(7′H)-one
CAS No.:1606589-75-6
Molecular Formula:C₂₈H₄₄O₅Si
Molecular Weight:488.74
Hs Code.:

Synonyms:(4a′S,5′S,8a′S)-5′-[2-(tert-butyldimethylsiloxy)-3-methoxybenzyl]-5′,8a′-dimethylhexahydro-2′Hspiro{[1,3]dioxolane-2,1′-naphthalen}-6′(7′H)-one

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Chemical Property of (4a′S,5′S,8a′S)-5′-[2-(tert-butyldimethylsiloxy)-3-methoxybenzyl]-5′,8a′-dimethylhexahydro-2′Hspiro{[1,3]dioxolane-2,1′-naphthalen}-6′(7′H)-one

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Technology Process of (4a′S,5′S,8a′S)-5′-[2-(tert-butyldimethylsiloxy)-3-methoxybenzyl]-5′,8a′-dimethylhexahydro-2′Hspiro{[1,3]dioxolane-2,1′-naphthalen}-6′(7′H)-one

There total 5 articles about (4a′S,5′S,8a′S)-5′-[2-(tert-butyldimethylsiloxy)-3-methoxybenzyl]-5′,8a′-dimethylhexahydro-2′Hspiro{[1,3]dioxolane-2,1′-naphthalen}-6′(7′H)-one 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: 81.0%

: (2-bromomethyl-6-methoxyphenoxy)(tert-butyl)dimethylsilane

: 26742-33-6
(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal

: 1606589-75-6
(4a′S,5′S,8a′S)-5′-[2-(tert-butyldimethylsiloxy)-3-methoxybenzyl]-5′,8a′-dimethylhexahydro-2′Hspiro{[1,3]dioxolane-2,1′-naphthalen}-6′(7′H)-one

Guidance literature:: (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal; With ammonia; lithium; In tetrahydrofuran; at -78 - -30 ℃; for 1h; Inert atmosphere;

(2-bromomethyl-6-methoxyphenoxy)(tert-butyl)dimethylsilane; With isoprene; In tetrahydrofuran; water; at -78 - 20 ℃; for 5h; Inert atmosphere;
DOI:10.1002/chem.201304809

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1606589-75-6
(4a′S,5′S,8a′S)-5′-[2-(tert-butyldimethylsiloxy)-3-methoxybenzyl]-5′,8a′-dimethylhexahydro-2′Hspiro{[1,3]dioxolane-2,1′-naphthalen}-6′(7′H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / water; tetrahydrofuran / 0.5 h / 0 °C

3.1: phosphorus tribromide / dichloromethane / 0 - 20 °C

4.1: lithium; ammonia / tetrahydrofuran / 1 h / -78 - -30 °C / Inert atmosphere

4.2: 5 h / -78 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; ammonia; phosphorus tribromide; lithium; In tetrahydrofuran; dichloromethane; water;
DOI:10.1002/chem.201304809

Reference yield:

: 5673-07-4
2,6-dimethoxytoluene

: 1606589-75-6
(4a′S,5′S,8a′S)-5′-[2-(tert-butyldimethylsiloxy)-3-methoxybenzyl]-5′,8a′-dimethylhexahydro-2′Hspiro{[1,3]dioxolane-2,1′-naphthalen}-6′(7′H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / water; tetrahydrofuran / 0.5 h / 0 °C

3.1: phosphorus tribromide / dichloromethane / 0 - 20 °C

4.1: lithium; ammonia / tetrahydrofuran / 1 h / -78 - -30 °C / Inert atmosphere

4.2: 5 h / -78 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; ammonia; phosphorus tribromide; lithium; In tetrahydrofuran; dichloromethane; water;
DOI:10.1002/chem.201304809