(2S,3R,4E,8Z,2'R)-1-(t-butyldiphenylsilyl)oxy-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadien-3-ol

Base Information

Chemical Name:(2S,3R,4E,8Z,2'R)-1-(t-butyldiphenylsilyl)oxy-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadien-3-ol
CAS No.:262593-00-0
Molecular Formula:C₅₀H₈₃NO₄Si
Molecular Weight:790.299
Hs Code.:

Synonyms:(2S,3R,4E,8Z,2'R)-1-(t-butyldiphenylsilyl)oxy-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadien-3-ol

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Chemical Property of (2S,3R,4E,8Z,2'R)-1-(t-butyldiphenylsilyl)oxy-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadien-3-ol

Chemical Property:

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Technology Process of (2S,3R,4E,8Z,2'R)-1-(t-butyldiphenylsilyl)oxy-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadien-3-ol

There total 7 articles about (2S,3R,4E,8Z,2'R)-1-(t-butyldiphenylsilyl)oxy-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadien-3-ol 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: 91.0%

: 115113-95-6
(2S,3R,4E,8Z,2'R)-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadiene-1,3-diol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 262593-00-0
(2S,3R,4E,8Z,2'R)-1-(t-butyldiphenylsilyl)oxy-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadien-3-ol

Guidance literature:: With 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4020(99)01018-2

Reference yield:

: 173531-24-3
(4S,1'S,2'R)-4-(1',2'-Epoxybut-3'-enyl)-2-phenyl-4,5-dihydrooxazole

: 262593-00-0
(2S,3R,4E,8Z,2'R)-1-(t-butyldiphenylsilyl)oxy-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadien-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / LDA; CuI / tetrahydrofuran / -70 - -10 °C

2: 91 percent / iBu₂AlH / toluene / 0.83 h / -70 - -50 °C

3: 78 percent / t-BuOK / tetrahydrofuran / -70 - 0 °C

4: 145 mg / aq. HCl / tetrahydrofuran / 16 h / 20 °C

5: 198 mg / Et₃N / dimethylformamide / 6 h / 60 °C

6: 94 percent / NaOMe / CH₂Cl₂; methanol / 1 h / 0 °C

7: 91 percent / imidazole / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

With 1H-imidazole; hydrogenchloride; copper(l) iodide; potassium tert-butylate; sodium methylate; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Ring cleavage / 2: Reduction / 3: Wittig olefination / 4: Ring cleavage / 5: Acylation / 6: Hydrolysis / 7: Substitution;
DOI:10.1016/S0040-4020(99)01018-2

Reference yield:

: 115031-70-4
Benzoic acid (4E,8Z)-(2S,3R)-2-amino-3-hydroxy-octadeca-4,8-dienyl ester; hydrochloride

: 262593-00-0
(2S,3R,4E,8Z,2'R)-1-(t-butyldiphenylsilyl)oxy-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadien-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 198 mg / Et₃N / dimethylformamide / 6 h / 60 °C

2: 94 percent / NaOMe / CH₂Cl₂; methanol / 1 h / 0 °C

3: 91 percent / imidazole / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

With 1H-imidazole; sodium methylate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrolysis / 3: Substitution;
DOI:10.1016/S0040-4020(99)01018-2