(3S,5R,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-dec-9-enoic acid

Base Information

Chemical Name:(3S,5R,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-dec-9-enoic acid
CAS No.:197233-14-0
Molecular Formula:C₄₄H₆₈O₅Si₃
Molecular Weight:761.277
Hs Code.:

Synonyms:(3S,5R,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-dec-9-enoic acid

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Chemical Property of (3S,5R,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-dec-9-enoic acid

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Technology Process of (3S,5R,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-dec-9-enoic acid

There total 17 articles about (3S,5R,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-dec-9-enoic acid 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:

: (3S,5R,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-dec-9-enoic acid tert-butyl ester

: 197233-14-0
(3S,5R,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-dec-9-enoic acid

Guidance literature:: With 2,6-dimethylpyridine; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at 20 ℃;
DOI:10.1021/ja971946k

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 197233-14-0
(3S,5R,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-dec-9-enoic acid

Guidance literature:: Multi-step reaction with 8 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: 76 percent / NaN(SiMe₃)2 / toluene / 0 - 20 °C

5.1: 85 percent / PhI(OCOCF₃)2 / CH₂Cl₂; acetonitrile; H₂O / 20 °C

6.1: tetrahydrofuran / 0 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 20 °C

8.1: TESOTf; 2,6-lutidine / CH₂Cl₂ / 20 °C

With 2,6-dimethylpyridine; oxalyl dichloride; triethylsilyl trifluoromethyl sulfonate; sodium hexamethyldisilazane; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; 1.1: silylation / 2.1: Oxidation / 3.1: Condensation / 3.2: Elimination / 4.1: Wittig reaction / 5.1: Ring cleavage / 6.1: Addition / 7.1: silylation / 8.1: dealkylation;
DOI:10.1021/ja971946k

Reference yield:

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

: 197233-14-0
(3S,5R,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-triphenylsilanyloxy-dec-9-enoic acid

Guidance literature:: Multi-step reaction with 16 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: 76 percent / NaN(SiMe₃)2 / toluene / 0 - 20 °C

13.1: 85 percent / PhI(OCOCF₃)2 / CH₂Cl₂; acetonitrile; H₂O / 20 °C

14.1: tetrahydrofuran / 0 °C

15.1: 2,6-lutidine / CH₂Cl₂ / 20 °C

16.1: TESOTf; 2,6-lutidine / CH₂Cl₂ / 20 °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; triethylsilyl trifluoromethyl sulfonate; sodium hexamethyldisilazane; titanium tetrachloride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 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: Ring cleavage / 14.1: Addition / 15.1: silylation / 16.1: dealkylation;
DOI:10.1021/ja971946k