(2R,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile

Base Information

Chemical Name:(2R,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile
CAS No.:1254331-78-6
Molecular Formula:C₂₇H₄₅NO₂Si₂
Molecular Weight:471.831
Hs Code.:

Synonyms:(2R,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile

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Chemical Property of (2R,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile

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Technology Process of (2R,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile

There total 7 articles about (2R,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile 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: 96.0%

: 1254331-79-7
(2S,4E)-2-tert-butyldimethylsilyloxy-5-phenylpent-4-enal

: 1254331-72-0
(S)-2-(tert-butyldimethylsilyloxy)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butanenitrile

: 1254331-78-6
(2R,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile

Guidance literature:: (S)-2-(tert-butyldimethylsilyloxy)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butanenitrile; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.75h;

(2S,4E)-2-tert-butyldimethylsilyloxy-5-phenylpent-4-enal; In tetrahydrofuran; at -78 - 20 ℃; for 3h; enantioselective reaction;
DOI:10.1021/acs.joc.8b02033

Reference yield: 88.2%

: 1254331-79-7
(2S,4E)-2-tert-butyldimethylsilyloxy-5-phenylpent-4-enal

: 1254331-90-2
(R)-2-(tert-butyldimethylsilyloxy)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butanenitrile

: 1254331-78-6
(2R,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile

Guidance literature:: (R)-2-(tert-butyldimethylsilyloxy)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butanenitrile; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.75h;

(2S,4E)-2-tert-butyldimethylsilyloxy-5-phenylpent-4-enal; In tetrahydrofuran; at -78 ℃; for 3h; stereoselective reaction;
DOI:10.1021/ol1021417

Reference yield:

: 1254331-89-9
(R)-2-(tert-butyldimethylsilyloxy)-4-(1-phenyl-1H-tetrazol-5-ylthio)butanenitrile

: 1254331-78-6
(2R,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile

Guidance literature:: Multi-step reaction with 2 steps

1.1: hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / ethanol; water / 24 h / 0 - 20 °C

2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C

2.2: 3 h / -78 - 20 °C

With hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide; potassium hexamethylsilazane; In tetrahydrofuran; ethanol; water; 2.1: |Julia-Kocienski Olefination / 2.2: |Julia-Kocienski Olefination;
DOI:10.1021/acs.joc.8b02033