(4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne

Base Information

Chemical Name:(4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne
CAS No.:693783-12-9
Molecular Formula:C₂₇H₄₄OSi₂
Molecular Weight:440.817
Hs Code.:

Synonyms:(4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne

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Chemical Property of (4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne

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Technology Process of (4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne

There total 3 articles about (4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne 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: 73.0%

: 762-72-1
allyl-trimethyl-silane

: 693782-99-9
(6S)-6-O-tert-butyldimethylsilyl-7-methyl-3-O-trimethylsilyl-1-trimethylsilyl-3-phenyl-(4E)-octen-1-yne-3,6-diol

: 693783-12-9
(4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -50 ℃; for 0.166667h;
DOI:10.1021/ol049847g

Reference yield:

: 762-72-1
allyl-trimethyl-silane

: 693782-99-9
(6S)-6-O-tert-butyldimethylsilyl-7-methyl-3-O-trimethylsilyl-1-trimethylsilyl-3-phenyl-(4E)-octen-1-yne-3,6-diol

: 693783-08-3
(4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne

: 693783-12-9
(4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -50 ℃; for 0.166667h;
DOI:10.1021/ol049847g

Reference yield:

: (Z)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-hex-2-en-1-one

: 693783-12-9
(4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne

Guidance literature:: Multi-step reaction with 2 steps

1.1: BuLi / tetrahydrofuran; hexane / 0 °C

1.2: tetrahydrofuran; hexane / 0 °C

1.3: 76 percent / tetrahydrofuran; hexane / 0 °C

2.1: TMSOTf / CH₂Cl₂ / 0.17 h / -50 °C

With n-butyllithium; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol049847g