(4S,5S)-3-(4-chlorophenyl)-5-[(S)-hydroxy(trimethylsilyl)methyl]-4-propyl-4,5-dihydroisoxazole

Base Information

Chemical Name:(4S,5S)-3-(4-chlorophenyl)-5-[(S)-hydroxy(trimethylsilyl)methyl]-4-propyl-4,5-dihydroisoxazole
CAS No.:233596-87-7
Molecular Formula:C₁₆H₂₄ClNO₂Si
Molecular Weight:325.911
Hs Code.:

Synonyms:(4S,5S)-3-(4-chlorophenyl)-5-[(S)-hydroxy(trimethylsilyl)methyl]-4-propyl-4,5-dihydroisoxazole

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Chemical Property of (4S,5S)-3-(4-chlorophenyl)-5-[(S)-hydroxy(trimethylsilyl)methyl]-4-propyl-4,5-dihydroisoxazole

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Technology Process of (4S,5S)-3-(4-chlorophenyl)-5-[(S)-hydroxy(trimethylsilyl)methyl]-4-propyl-4,5-dihydroisoxazole

There total 4 articles about (4S,5S)-3-(4-chlorophenyl)-5-[(S)-hydroxy(trimethylsilyl)methyl]-4-propyl-4,5-dihydroisoxazole 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: 52.0%

: 233596-85-5
trans-(S)-1-trimethylsilyl-2-hexen-1-ol

: 28123-63-9
4-chlorobenzohydroximoyl chloride

: 233596-87-7
(4S,5S)-3-(4-chlorophenyl)-5-[(S)-hydroxy(trimethylsilyl)methyl]-4-propyl-4,5-dihydroisoxazole

Guidance literature:: With bromo magnesium butylate; triethylamine; In dichloromethane; at -78 - 20 ℃; for 17h;
DOI:10.1016/S0040-4039(99)00688-7

Reference yield:

: 233596-85-5
trans-(S)-1-trimethylsilyl-2-hexen-1-ol

: 28123-63-9
4-chlorobenzohydroximoyl chloride

: 233596-87-7
(4S,5S)-3-(4-chlorophenyl)-5-[(S)-hydroxy(trimethylsilyl)methyl]-4-propyl-4,5-dihydroisoxazole

: (4R,5R)-3-(4-chlorophenyl)-5-[(R)-hydroxy(trimethylsilyl)methyl]-4-propyl-4,5-dihydroisoxazole

Guidance literature:: With methylmagnesium bromide; triethylamine; butan-1-ol; In diethyl ether; dichloromethane; at -78 - 20 ℃; for 17h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4020(02)01255-3

Reference yield:

: 928-95-0
(E)-2-Hexen-1-ol

: 233596-87-7
(4S,5S)-3-(4-chlorophenyl)-5-[(S)-hydroxy(trimethylsilyl)methyl]-4-propyl-4,5-dihydroisoxazole

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / 2.5 h / -78 °C

1.3: 68 percent / sec-BuLi / tetrahydrofuran / 2 h / -78 °C

2.1: (-)-B-chlorodiisopinocampheylborane / tetrahydrofuran / 20 h / -10 °C

3.1: methylmagnesium bromide; BuOH; Et₃N / diethyl ether; CH₂Cl₂ / 17 h / -78 - 20 °C

With n-butyllithium; methylmagnesium bromide; triethylamine; (-)-diisopinocamphenylborane chloride; butan-1-ol; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(02)01255-3