(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-<(p-tolylsulfonyl)oxy>dodecane

Base Information

Chemical Name:(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-<(p-tolylsulfonyl)oxy>dodecane
CAS No.:131618-41-2
Molecular Formula:C₃₈H₆₆O₆SSi₂
Molecular Weight:707.175
Hs Code.:

Synonyms:(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-<(p-tolylsulfonyl)oxy>dodecane

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Chemical Property of (5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-<(p-tolylsulfonyl)oxy>dodecane

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Technology Process of (5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-<(p-tolylsulfonyl)oxy>dodecane

There total 6 articles about (5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-<(p-tolylsulfonyl)oxy>dodecane 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: 100.0%

: 131618-40-1
(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-dodecanol

: 98-59-9
p-toluenesulfonyl chloride

: 131618-41-2
(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-<(p-tolylsulfonyl)oxy>dodecane

Guidance literature:: With dmap; In dichloromethane;
DOI:10.1016/S0040-4039(00)94464-2

Reference yield:

: 2,5-bis(methylsulfonyloxy)-1,6-hexanediol

: 131618-41-2
(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-<(p-tolylsulfonyl)oxy>dodecane

Guidance literature:: Multi-step reaction with 6 steps

1: 20percent KOH / methanol / 1 h / ice bath

2: 62 percent / CuI / tetrahydrofuran / 1.5 h / -15 °C

3: 91 percent / imidazole / dimethylformamide / 5 h / Ambient temperature

4: 90 percent / H₂ / 10percent Pd/C / methanol / 5 h

5: 1.) NaH / 1.) DMSO, THF, r.t., 1 h, 2.) THF, 70-80 deg C, 1.5 h

6: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

With 1H-imidazole; dmap; potassium hydroxide; copper(l) iodide; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00004a011

Reference yield:

: 131618-31-0
(5S,8S)-1,12-Bis(benzyloxy)-5,8-dodecanediol

: 131618-41-2
(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-<(p-tolylsulfonyl)oxy>dodecane

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / imidazole / dimethylformamide / 5 h / Ambient temperature

2: 90 percent / H₂ / 10percent Pd/C / methanol / 5 h

3: 1.) NaH / 1.) DMSO, THF, r.t., 1 h, 2.) THF, 70-80 deg C, 1.5 h

4: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

With 1H-imidazole; dmap; hydrogen; sodium hydride; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00004a011