(2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-ol

Base Information

Chemical Name:(2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-ol
CAS No.:852834-08-3
Molecular Formula:C₃₉H₆₆O₄Si₃
Molecular Weight:683.207
Hs Code.:

Synonyms:(2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-ol

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Chemical Property of (2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-ol

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Technology Process of (2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-ol

There total 6 articles about (2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-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: 76.0%

: 852834-07-2
(5S)-7-(tert-butyldiphenylsilyloxy)-5-(tert-butyldimethylsilyloxy)heptanal

: C₁₀H₁₉LiOSi

: 852834-08-3
(2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-ol

Guidance literature:: With lithium bromide; In tetrahydrofuran; at -78 ℃;
DOI:10.1039/b418106a

Reference yield: 76.0%

: 852834-07-2
(5S)-7-(tert-butyldiphenylsilyloxy)-5-(tert-butyldimethylsilyloxy)heptanal

: 193812-02-1
(R)-(but-3-yn-2-yloxy)(tert-butyl)dimethylsilane

: 852834-08-3
(2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-ol

Guidance literature:: (R)-(but-3-yn-2-yloxy)(tert-butyl)dimethylsilane; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

With lithium bromide; In tetrahydrofuran; at -78 ℃; for 0.25h;

(5S)-7-(tert-butyldiphenylsilyloxy)-5-(tert-butyldimethylsilyloxy)heptanal; In tetrahydrofuran; at -78 ℃; for 5h; Further stages.;
DOI:10.1039/b708265g

Reference yield:

: 1-(tert-butyl-diphenyl-silanyloxy)-hept-6-en-3-ol

: 852834-08-3
(2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / imidazole; DMAP / CH₂Cl₂

2.1: BH₃*SMe₂ / tetrahydrofuran / 0 °C

2.2: 83 percent / aq. NaOH; H₂O₂

3.1: 86 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

4.1: 76 percent / LiBr / tetrahydrofuran / -78 °C

With pyridine; 1H-imidazole; dmap; dimethylsulfide borane complex; Dess-Martin periodane; lithium bromide; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b418106a