(3S,11R,12S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10,12-dimethyl-1-(toluene-4-sulfonyl)-tetradec-8-yn-7-one

Base Information

Chemical Name:(3S,11R,12S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10,12-dimethyl-1-(toluene-4-sulfonyl)-tetradec-8-yn-7-one
CAS No.:106006-04-6
Molecular Formula:C₃₅H₆₂O₆SSi₂
Molecular Weight:667.111
Hs Code.:

Synonyms:(3S,11R,12S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10,12-dimethyl-1-(toluene-4-sulfonyl)-tetradec-8-yn-7-one

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Chemical Property of (3S,11R,12S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10,12-dimethyl-1-(toluene-4-sulfonyl)-tetradec-8-yn-7-one

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Technology Process of (3S,11R,12S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10,12-dimethyl-1-(toluene-4-sulfonyl)-tetradec-8-yn-7-one

There total 16 articles about (3S,11R,12S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10,12-dimethyl-1-(toluene-4-sulfonyl)-tetradec-8-yn-7-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: 45.0%

: 105989-28-4
(6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-5,7-dimethyl-non-3-yn-2-one

: 105989-29-5
(S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentanal

: 106006-04-6
(3S,11R,12S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10,12-dimethyl-1-(toluene-4-sulfonyl)-tetradec-8-yn-7-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(00)85191-6

Reference yield:

: 1565-80-6
(2S)-2-methyl-1-butanol

: 106006-04-6
(3S,11R,12S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10,12-dimethyl-1-(toluene-4-sulfonyl)-tetradec-8-yn-7-one

Guidance literature:: Multi-step reaction with 10 steps

2: 62 percent / LDA / -78 °C

3: baker's yeast, glucose, 2 days

4: 1) LDA / 1) -50 deg C, THF, 2 h; 2) 5 percent HMPA, -50 deg C, 30 min

5: 93 percent / imidazole / dimethylformamide

6: 70 percent / DIBAL / diethyl ether / 0 °C

7: 70 percent / PCC

8: 1) PPh₃, 2) n-BuLi / 1) CH₂Cl₂ 2) -78 deg C, THF

9: BF₃*Et₂O / 1) -78 deg C, 10 min 2) -78 deg C 30 min

10: 45 percent / LDA / tetrahydrofuran / -78 °C

With 1H-imidazole; n-butyllithium; boron trifluoride diethyl etherate; diisobutylaluminium hydride; triphenylphosphine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)85191-6

Reference yield:

: 104629-71-2
(R)-(3-tert-butyldimethylsiloxy)-5-(pivaloyloxy)-1-pentanol

: 106006-04-6
(3S,11R,12S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-10,12-dimethyl-1-(toluene-4-sulfonyl)-tetradec-8-yn-7-one

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / NBS, PPh₃ / CH₂Cl₂

2: 71 percent / dimethylformamide

3: 99 percent / NaOH, MeOH

4: 82 percent / PCC, molecular sieves 3A / CH₂Cl₂

5: 45 percent / LDA / tetrahydrofuran / -78 °C

With methanol; sodium hydroxide; N-Bromosuccinimide; 3 A molecular sieve; triphenylphosphine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)85191-6