((2S,4aS,5S)-decahydro-1,1,4a-trimethyl-6-methylene-5-((E)-2-(phenylsulfonyl)vinyl)naphthalen-2-yloxy)(tert-butyl)dimethylsilane

Base Information

Chemical Name:((2S,4aS,5S)-decahydro-1,1,4a-trimethyl-6-methylene-5-((E)-2-(phenylsulfonyl)vinyl)naphthalen-2-yloxy)(tert-butyl)dimethylsilane
CAS No.:1352318-83-2
Molecular Formula:C₂₈H₄₄O₃SSi
Molecular Weight:488.807
Hs Code.:

Synonyms:((2S,4aS,5S)-decahydro-1,1,4a-trimethyl-6-methylene-5-((E)-2-(phenylsulfonyl)vinyl)naphthalen-2-yloxy)(tert-butyl)dimethylsilane

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Chemical Property of ((2S,4aS,5S)-decahydro-1,1,4a-trimethyl-6-methylene-5-((E)-2-(phenylsulfonyl)vinyl)naphthalen-2-yloxy)(tert-butyl)dimethylsilane

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Technology Process of ((2S,4aS,5S)-decahydro-1,1,4a-trimethyl-6-methylene-5-((E)-2-(phenylsulfonyl)vinyl)naphthalen-2-yloxy)(tert-butyl)dimethylsilane

There total 1 articles about ((2S,4aS,5S)-decahydro-1,1,4a-trimethyl-6-methylene-5-((E)-2-(phenylsulfonyl)vinyl)naphthalen-2-yloxy)(tert-butyl)dimethylsilane 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:

: 856683-46-0
(1S,4aR,6S,8aS)-6-(tert-Butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalene-1-carbaldehyde

: 56069-39-7
diethyl phenylsulfonylmethylphosphonate

: 1352318-83-2
((2S,4aS,5S)-decahydro-1,1,4a-trimethyl-6-methylene-5-((E)-2-(phenylsulfonyl)vinyl)naphthalen-2-yloxy)(tert-butyl)dimethylsilane

Guidance literature:: diethyl phenylsulfonylmethylphosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Inert atmosphere;

(1S,4aR,6S,8aS)-6-(tert-Butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalene-1-carbaldehyde; In tetrahydrofuran; hexane; for 12h; Inert atmosphere;
DOI:10.1021/jo201968t

Reference yield: 96.0%

: 1352318-83-2
((2S,4aS,5S)-decahydro-1,1,4a-trimethyl-6-methylene-5-((E)-2-(phenylsulfonyl)vinyl)naphthalen-2-yloxy)(tert-butyl)dimethylsilane

: 1352318-84-3
((2S,4aS,5S)-decahydro-1,1,4a-trimethyl-6-methylene-5-((E)-2-(phenylsulfonyl)ethyl)naphthalen-2-yloxy)(tert-butyl)dimethylsilane

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jo201968t

Reference yield:

: 1352318-83-2
((2S,4aS,5S)-decahydro-1,1,4a-trimethyl-6-methylene-5-((E)-2-(phenylsulfonyl)vinyl)naphthalen-2-yloxy)(tert-butyl)dimethylsilane

: C₃₉H₇₂O₆Si

Guidance literature:: Multi-step reaction with 10 steps

1.1: lithium triethylborohydride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.1: borane-THF / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

2.2: 4 h / 0 - 20 °C

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 20 °C

4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 0.17 h / Inert atmosphere

5.1: lithium; ethylamine / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C / Inert atmosphere

6.2: -60 - 0 °C / Inert atmosphere

7.1: tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

8.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 20 °C

9.1: tetrahydrofuran / 17 h / 0 °C

10.1: acetic acid / water / 4 h / 20 °C

With n-butyllithium; borane-THF; oxalyl dichloride; lithium; lithium triethylborohydride; Dess-Martin periodane; ethylamine; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; 2.1: Hydroboration reaction;
DOI:10.1021/jo201968t