(3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-undec-10-enoic acid tert-butyl ester

Base Information

Chemical Name:(3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-undec-10-enoic acid tert-butyl ester
CAS No.:197233-27-5
Molecular Formula:C₄₃H₆₄O₅Si₂
Molecular Weight:717.149
Hs Code.:

Synonyms:(3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-undec-10-enoic acid tert-butyl ester

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Chemical Property of (3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-undec-10-enoic acid tert-butyl ester

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Technology Process of (3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-undec-10-enoic acid tert-butyl ester

There total 18 articles about (3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-undec-10-enoic acid tert-butyl ester 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: 63.0%

: 540-88-5
acetic acid tert-butyl ester

: 197233-26-4
(3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-3-triphenylsilanyloxy-non-8-enal

: (3R,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-undec-10-enoic acid tert-butyl ester

: 197233-27-5
(3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-undec-10-enoic acid tert-butyl ester

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.333333h;
DOI:10.1021/ja971946k

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 197233-27-5
(3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-undec-10-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 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: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C

5.1: 99 percent / pTSA*H₂O / dioxane; H₂O / 2 h / 50 °C

6.1: 76 percent / tetrahydrofuran / 1 h / 0 - 20 °C

7.1: 92 percent / [bis(trifluoroacetoxy)iodobenzene] / tetrahydrofuran / 0.25 h / 20 °C

8.1: 81 percent / p-TSA*H₂O / dioxane; H₂O / 2 h / 55 °C

9.1: 63 percent / LDA / tetrahydrofuran / 0.33 h / -78 °C

With 2,6-dimethylpyridine; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 1.1: silylation / 2.1: Oxidation / 3.1: Condensation / 3.2: Elimination / 4.1: Wittig reaction / 5.1: Hydrolysis / 6.1: Wittig reaction / 7.1: Ring cleavage / 8.1: Hydrolysis / 9.1: Addition;
DOI:10.1021/ja971946k

Reference yield:

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

: 197233-27-5
(3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-undec-10-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 17 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: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C

13.1: 99 percent / pTSA*H₂O / dioxane; H₂O / 2 h / 50 °C

14.1: 76 percent / tetrahydrofuran / 1 h / 0 - 20 °C

15.1: 92 percent / [bis(trifluoroacetoxy)iodobenzene] / tetrahydrofuran / 0.25 h / 20 °C

16.1: 81 percent / p-TSA*H₂O / dioxane; H₂O / 2 h / 55 °C

17.1: 63 percent / LDA / tetrahydrofuran / 0.33 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; N-iodo-succinimide; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; diethylzinc; tri-n-butyl-tin hydride; titanium tetrachloride; toluene-4-sulfonic acid; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; 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: Wittig reaction / 13.1: Hydrolysis / 14.1: Wittig reaction / 15.1: Ring cleavage / 16.1: Hydrolysis / 17.1: Addition;
DOI:10.1021/ja971946k