(4S,6Z,8S,9R,10S)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)methoxy]-4,6,8,10-tetramethyl-6-undecen-3-one

Base Information

Chemical Name:(4S,6Z,8S,9R,10S)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)methoxy]-4,6,8,10-tetramethyl-6-undecen-3-one
CAS No.:522665-50-5
Molecular Formula:C₂₉H₅₀O₄Si
Molecular Weight:490.799
Hs Code.:

Synonyms:(4S,6Z,8S,9R,10S)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)methoxy]-4,6,8,10-tetramethyl-6-undecen-3-one

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Chemical Property of (4S,6Z,8S,9R,10S)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)methoxy]-4,6,8,10-tetramethyl-6-undecen-3-one

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Technology Process of (4S,6Z,8S,9R,10S)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)methoxy]-4,6,8,10-tetramethyl-6-undecen-3-one

There total 9 articles about (4S,6Z,8S,9R,10S)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)methoxy]-4,6,8,10-tetramethyl-6-undecen-3-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: 90.0%

: 925-90-6
ethylmagnesium bromide

: 522665-56-1
(2S,4Z,6S,7R,8S)-7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9-[(4-methoxyphenyl)methoxy]-2,4,6,8-tetramethyl-4-nonenoic acid methyl ester

: 522665-50-5
(4S,6Z,8S,9R,10S)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)methoxy]-4,6,8,10-tetramethyl-6-undecen-3-one

Guidance literature:: With N,O-dimethylhydroxylamine*hydrochloride; In tetrahydrofuran; at -10 - 20 ℃;
DOI:10.1021/ol034186t

Reference yield: 75.0%

: 925-90-6
ethylmagnesium bromide

: 522665-57-2
(2S,4Z,6S,7R,8S)-7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-N-methoxy-9-[(4-methoxyphenyl)methoxy]-N,2,4,6,8-pentamethyl-4-nonenamide

: 522665-50-5
(4S,6Z,8S,9R,10S)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)methoxy]-4,6,8,10-tetramethyl-6-undecen-3-one

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/ol034186t

Reference yield:

: 132969-60-9
(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal

: 522665-50-5
(4S,6Z,8S,9R,10S)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-[(4-methoxyphenyl)methoxy]-4,6,8,10-tetramethyl-6-undecen-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 58 percent / molecular sieves 4 Angstroem / toluene / 18 h / -78 °C

2.1: 95 percent / 2,6-lutidine / tetrahydrofuran / 1.5 h / 0 °C

3.1: 4-methylmorpholine N-oxide; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 18 h / 20 °C

3.2: 71 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

4.1: 87 percent / Pd(PPh₃)4 / tetrahydrofuran / 18 h / 20 °C

5.1: 90 percent / N,O-dimethylhydroxylamine hydrochloride / tetrahydrofuran / -10 - 20 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; 4 A molecular sieve; N,O-dimethylhydroxylamine*hydrochloride; 4-methylmorpholine N-oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; acetone; toluene; tert-butyl alcohol; 5.1: Negishi cross-coupling;
DOI:10.1021/ol034186t