(3R,4S,6R,7S,9S)-4-(tert-butyldimethylsilyloxy)-10-(4-methoxyphenoxy)-3,6,9-trimethyl-6,7-bis[(triethylsilyl)oxy]dec-1-ene

Base Information

Chemical Name:(3R,4S,6R,7S,9S)-4-(tert-butyldimethylsilyloxy)-10-(4-methoxyphenoxy)-3,6,9-trimethyl-6,7-bis[(triethylsilyl)oxy]dec-1-ene
CAS No.:944943-22-0
Molecular Formula:C₃₉H₇₆O₅Si₃
Molecular Weight:709.286
Hs Code.:

Synonyms:(3R,4S,6R,7S,9S)-4-(tert-butyldimethylsilyloxy)-10-(4-methoxyphenoxy)-3,6,9-trimethyl-6,7-bis[(triethylsilyl)oxy]dec-1-ene

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Chemical Property of (3R,4S,6R,7S,9S)-4-(tert-butyldimethylsilyloxy)-10-(4-methoxyphenoxy)-3,6,9-trimethyl-6,7-bis[(triethylsilyl)oxy]dec-1-ene

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Technology Process of (3R,4S,6R,7S,9S)-4-(tert-butyldimethylsilyloxy)-10-(4-methoxyphenoxy)-3,6,9-trimethyl-6,7-bis[(triethylsilyl)oxy]dec-1-ene

There total 7 articles about (3R,4S,6R,7S,9S)-4-(tert-butyldimethylsilyloxy)-10-(4-methoxyphenoxy)-3,6,9-trimethyl-6,7-bis[(triethylsilyl)oxy]dec-1-ene 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: 93.0%

: 944943-20-8
(2S,3S,5R,6S,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanal

: 1779-49-3
Methyltriphenylphosphonium bromide

: 944943-22-0
(3R,4S,6R,7S,9S)-4-(tert-butyldimethylsilyloxy)-10-(4-methoxyphenoxy)-3,6,9-trimethyl-6,7-bis[(triethylsilyl)oxy]dec-1-ene

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -10 - 0 ℃;
DOI:10.1021/ol0710360

Reference yield:

: 944942-96-5
(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol

: 944943-22-0
(3R,4S,6R,7S,9S)-4-(tert-butyldimethylsilyloxy)-10-(4-methoxyphenoxy)-3,6,9-trimethyl-6,7-bis[(triethylsilyl)oxy]dec-1-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

2.1: triethylamine / CH₂Cl₂; hexane / 1 h / -78 °C

2.2: CH₂Cl₂; hexane / -78 - 20 °C

2.3: 84 percent / methanol; hydrogen peroxide / CH₂Cl₂; hexane

3.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

4.1: 80 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 3 h / -78 °C

5.1: 96 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

6.1: 93 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / -10 - 0 °C

With 2,6-dimethylpyridine; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: Dess-Martin oxidation / 5.1: Dess-Martin oxidation;
DOI:10.1021/ol0710360

Reference yield:

: 944943-16-2
(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6S,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

: 944943-22-0
(3R,4S,6R,7S,9S)-4-(tert-butyldimethylsilyloxy)-10-(4-methoxyphenoxy)-3,6,9-trimethyl-6,7-bis[(triethylsilyl)oxy]dec-1-ene

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 3 h / -78 °C

2: 96 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

3: 93 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / -10 - 0 °C

With potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; toluene; 2: Dess-Martin oxidation;
DOI:10.1021/ol0710360