(4S,5S)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol

Base Information

Chemical Name:(4S,5S)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol
CAS No.:366785-19-5
Molecular Formula:C₃₇H₆₃NO₂Si
Molecular Weight:581.998
Hs Code.:

Synonyms:(4S,5S)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol

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Chemical Property of (4S,5S)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol

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Technology Process of (4S,5S)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol

There total 4 articles about (4S,5S)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol 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: 76.0%

: 366785-12-8
(4S)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanone

: 366785-11-7
(4S,5R)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol

: 366785-19-5
(4S,5S)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -20 ℃; for 2h;
DOI:10.1016/S0957-4166(01)00251-8

Reference yield:

: 15890-72-9
laurylmagnesium bromide

: 366785-19-5
(4S,5S)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / diethyl ether / 1.5 h / 0 °C

2: 86 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 20 °C

3: 76 percent / sodium borohydride / methanol; tetrahydrofuran / 2 h / -20 °C

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2: Swern oxidation;
DOI:10.1016/S0957-4166(01)00251-8

Reference yield:

: 205068-02-6
(-)-S-5-(tert-butyldimethylsilyloxy)-2-(N,N-dibenzylamino)-1-pentanal

: 366785-19-5
(4S,5S)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / diethyl ether / 1.5 h / 0 °C

2: 86 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 20 °C

3: 76 percent / sodium borohydride / methanol; tetrahydrofuran / 2 h / -20 °C

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2: Swern oxidation;
DOI:10.1016/S0957-4166(01)00251-8