(3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6,10-pentamethyl-3-triphenylsilanyloxy-undec-10-enal

Base Information

Chemical Name:(3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6,10-pentamethyl-3-triphenylsilanyloxy-undec-10-enal
CAS No.:197233-34-4
Molecular Formula:C₄₀H₅₈O₃Si₂
Molecular Weight:643.07
Hs Code.:

Synonyms:(3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6,10-pentamethyl-3-triphenylsilanyloxy-undec-10-enal

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Chemical Property of (3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6,10-pentamethyl-3-triphenylsilanyloxy-undec-10-enal

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Technology Process of (3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6,10-pentamethyl-3-triphenylsilanyloxy-undec-10-enal

There total 15 articles about (3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6,10-pentamethyl-3-triphenylsilanyloxy-undec-10-enal 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: 95.0%

: 197233-33-3
2-[(2R,3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-1,1,3,5,9-pentamethyl-2-triphenylsilanyloxy-dec-9-enyl]-[1,3]dithiane

: 197233-34-4
(3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6,10-pentamethyl-3-triphenylsilanyloxy-undec-10-enal

Guidance literature:: 2-[(2R,3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-1,1,3,5,9-pentamethyl-2-triphenylsilanyloxy-dec-9-enyl]-[1,3]dithiane; With bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; at 20 ℃; for 0.25h;

With toluene-4-sulfonic acid; In 1,4-dioxane; water; at 50 ℃; for 2h;
DOI:10.1021/ja971946k

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 197233-34-4
(3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6,10-pentamethyl-3-triphenylsilanyloxy-undec-10-enal

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

3.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

3.2: 90 percent / Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: tert-butyllithium / diethyl ether / 0.5 h / -78 °C

4.2: 89 percent / diethyl ether / 0.58 h / -78 - 0 °C

5.1: thiocarbonyl diimidazole; 4-DMAP / tetrahydrofuran / 2 h / 90 °C

5.2: 0.823 g / n-Bu₃SnH; AIBN / benzene / 1 h / 80 °C

6.1: [bis(trifluoroacetoxy)iodobenzene] / methanol; tetrahydrofuran / 0.25 h / 20 °C

6.2: 95 percent / pTSA*H₂O / dioxane; H₂O / 2 h / 50 °C

With 2,6-dimethylpyridine; dmap; oxalyl dichloride; tert.-butyl lithium; di(1H-imidazol-2-yl)methanethione; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1.1: silylation / 2.1: Oxidation / 3.1: Condensation / 3.2: Elimination / 4.1: Metallation / 4.2: Addition / 5.1: Addition / 5.2: Reduction / 6.1: Oxidation / 6.2: Hydrolysis;
DOI:10.1021/ja971946k

Reference yield:

: 72486-93-2
1-methoxy-2-methyl-3-trimethylsiloxy-1,3-pentadiene

: 197233-34-4
(3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6,10-pentamethyl-3-triphenylsilanyloxy-undec-10-enal

Guidance literature:: Multi-step reaction with 14 steps

1.1: TiCl₄ / CH₂Cl₂ / -78 °C

2.1: CSA / benzene / 20 °C

3.1: 91 percent / LiAlH₄ / diethyl ether / -78 °C

4.1: 93 percent / Et₂Zn / diethyl ether / 20 °C

5.1: N-iodosuccinimide / 20 °C

6.1: n-Bu₃SnH; AIBN / benzene / Heating

7.1: 97 percent / imidazole / dimethylformamide / 20 °C

8.1: 78 percent / TiCl₄ / CH₂Cl₂ / -78 - -40 °C

9.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

10.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

11.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

11.2: 90 percent / Et₃N / CH₂Cl₂ / -78 - 0 °C

12.1: tert-butyllithium / diethyl ether / 0.5 h / -78 °C

12.2: 89 percent / diethyl ether / 0.58 h / -78 - 0 °C

13.1: thiocarbonyl diimidazole; 4-DMAP / tetrahydrofuran / 2 h / 90 °C

13.2: 0.823 g / n-Bu₃SnH; AIBN / benzene / 1 h / 80 °C

14.1: [bis(trifluoroacetoxy)iodobenzene] / methanol; tetrahydrofuran / 0.25 h / 20 °C

14.2: 95 percent / pTSA*H₂O / dioxane; H₂O / 2 h / 50 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tert.-butyl lithium; diethylzinc; tri-n-butyl-tin hydride; titanium tetrachloride; di(1H-imidazol-2-yl)methanethione; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1.1: Cycloaddition / 2.1: acidolysis / 3.1: Reduction / 4.1: Cycloaddition / 5.1: Ring cleavage / 6.1: Dehalogenation / 7.1: silylation / 8.1: Condensation / 9.1: silylation / 10.1: Oxidation / 11.1: Condensation / 11.2: Elimination / 12.1: Metallation / 12.2: Addition / 13.1: Addition / 13.2: Reduction / 14.1: Oxidation / 14.2: Hydrolysis;
DOI:10.1021/ja971946k