(4S,5S)-5-[(S)-hydroxy(trimethylsilyl)methyl]-3-(2-phenylethyl)-4-propyl-4,5-dihydroisoxazole

Base Information

• Chemical Name: (4S,5S)-5-[(S)-hydroxy(trimethylsilyl)methyl]-3-(2-phenylethyl)-4-propyl-4,5-dihydroisoxazole
• CAS No.: 233596-88-8
• Molecular Formula: C₁₈H₂₉NO₂Si
• Molecular Weight: 319.519
• Mol file: 233596-88-8.mol

Synonyms:(4S,5S)-5-[(S)-hydroxy(trimethylsilyl)methyl]-3-(2-phenylethyl)-4-propyl-4,5-dihydroisoxazole

Chemical Property of (4S,5S)-5-[(S)-hydroxy(trimethylsilyl)methyl]-3-(2-phenylethyl)-4-propyl-4,5-dihydroisoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-5-[(S)-hydroxy(trimethylsilyl)methyl]-3-(2-phenylethyl)-4-propyl-4,5-dihydroisoxazole

There total 4 articles about (4S,5S)-5-[(S)-hydroxy(trimethylsilyl)methyl]-3-(2-phenylethyl)-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: 40.0%

N-hydroxy(2-phenylethyl)-oximidoyl chloride (92988-96-0) + trans-(S)-1-trimethylsilyl-2-hexen-1-ol (233596-85-5) → (4S,5S)-5-[(S)-hydroxy(trimethylsilyl)methyl]-3-(2-phenylethyl)-4-propyl-4,5-dihydroisoxazole (233596-88-8)

Guidance literature:

With bromo magnesium butylate; triethylamine; In dichloromethane; at -78 - 20 ℃; for 17h;

DOI:10.1016/S0040-4039(99)00688-7

Reference yield:

N-hydroxy(2-phenylethyl)-oximidoyl chloride (92988-96-0) + trans-(S)-1-trimethylsilyl-2-hexen-1-ol (233596-85-5) → (4S,5S)-5-[(S)-hydroxy(trimethylsilyl)methyl]-3-(2-phenylethyl)-4-propyl-4,5-dihydroisoxazole (233596-88-8) + (4R,5R)-5-[(R)-hydroxy(trimethylsilyl)methyl]-3-(2-phenylethyl)-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:

(E)-2-Hexen-1-ol (928-95-0) → (4S,5S)-5-[(S)-hydroxy(trimethylsilyl)methyl]-3-(2-phenylethyl)-4-propyl-4,5-dihydroisoxazole (233596-88-8)

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

upstream raw materials:

N-hydroxy(2-phenylethyl)-oximidoyl chloride

trans-(S)-1-trimethylsilyl-2-hexen-1-ol

(E)-2-Hexen-1-ol

(+/-)-1-(1-hexenyl)-1-(trimethylsilyl)methanol

Downstream raw materials:

3-phenethyl-4-propyl-5,6-dihydro-4H-[1,2]oxazin-6-ol