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

Base Information

Chemical Name:(2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-one
CAS No.:852834-14-1
Molecular Formula:C₃₉H₆₄O₄Si₃
Molecular Weight:681.191
Hs Code.:

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

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

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

There total 6 articles about (2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-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: 87.0%

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

: 852834-14-1
(2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-one

Guidance literature:: With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1039/b708265g

Reference yield:

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

: 852834-14-1
(2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-one

Guidance literature:: Multi-step reaction with 5 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

5.1: 78 percent / tetrapropylammonium perruthenate; NMO / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; dimethylsulfide borane complex; Dess-Martin periodane; lithium bromide; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b418106a

Reference yield:

: 852834-06-1
(3S)-1-(tert-butyldiphenylsilyloxy)-3-(tert-butyldimethylsilyloxy)hept-6-ene

: 852834-14-1
(2R,9S)-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-3-yn-5-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 0 °C

1.2: 83 percent / aq. NaOH; H₂O₂

2.1: 86 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

3.1: 76 percent / LiBr / tetrahydrofuran / -78 °C

4.1: 78 percent / tetrapropylammonium perruthenate; NMO / CH₂Cl₂

With pyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; dimethylsulfide borane complex; Dess-Martin periodane; lithium bromide; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b418106a