ethyl (5R,6S)-5,6-epoxy-5-{[(tert-butyldiphenylsilyl)oxy]methyl}hexadecanoate

Base Information

Chemical Name:ethyl (5R,6S)-5,6-epoxy-5-{[(tert-butyldiphenylsilyl)oxy]methyl}hexadecanoate
CAS No.:796105-50-5
Molecular Formula:C₃₅H₅₄O₄Si
Molecular Weight:566.897
Hs Code.:

Synonyms:ethyl (5R,6S)-5,6-epoxy-5-{[(tert-butyldiphenylsilyl)oxy]methyl}hexadecanoate

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Chemical Property of ethyl (5R,6S)-5,6-epoxy-5-{[(tert-butyldiphenylsilyl)oxy]methyl}hexadecanoate

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Technology Process of ethyl (5R,6S)-5,6-epoxy-5-{[(tert-butyldiphenylsilyl)oxy]methyl}hexadecanoate

There total 9 articles about ethyl (5R,6S)-5,6-epoxy-5-{[(tert-butyldiphenylsilyl)oxy]methyl}hexadecanoate 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%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 796105-49-2
ethyl (5R,6S)-5,6-epoxy-5-(hydroxymethyl)hexadecanoate

: 796105-50-5
ethyl (5R,6S)-5,6-epoxy-5-{[(tert-butyldiphenylsilyl)oxy]methyl}hexadecanoate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 13h;
DOI:10.1246/bcsj.78.1549

Reference yield:

: 74962-98-4,68480-25-1
trans-2-tridecenol

: 796105-50-5
ethyl (5R,6S)-5,6-epoxy-5-{[(tert-butyldiphenylsilyl)oxy]methyl}hexadecanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / pyridine / CHCl₃ / 0 - 20 °C

2.1: 95 percent / pyridine*HBr₃; AcOH / 3 h / 20 °C

3.1: DBU / dimethylformamide / 1.5 h / 60 °C

3.2: 361 mg / LiOH / dioxane; H₂O / 0.5 h / 20 °C

4.1: 98 percent / iPr₂NEt / CH₂Cl₂ / 20 h / 0 °C

5.1: 73 percent / [PdCl₂(dppf)] / toluene; tetrahydrofuran / 1 h / 90 °C

6.1: 80 percent / HCl / ethanol / 7 h / 50 °C

7.1: D-(-)-DET; TBHP; Ti(OiPr)4 / molecular sieves 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / 10 h / -30 °C

8.1: 100 percent / imidazole / dimethylformamide / 13 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; pyridinium perbromide hydrobromide; diethyl (2S,3S)-tartrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 7.1: Sharpless asymmetric epoxidation;
DOI:10.1246/bcsj.78.1549

Reference yield:

: 796105-40-3
(E)-1-[(benzyloxy)methoxy]-2-bromotridec-2-ene

: 796105-50-5
ethyl (5R,6S)-5,6-epoxy-5-{[(tert-butyldiphenylsilyl)oxy]methyl}hexadecanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 73 percent / [PdCl₂(dppf)] / toluene; tetrahydrofuran / 1 h / 90 °C

2: 80 percent / HCl / ethanol / 7 h / 50 °C

3: D-(-)-DET; TBHP; Ti(OiPr)4 / molecular sieves 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / 10 h / -30 °C

4: 100 percent / imidazole / dimethylformamide / 13 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Sharpless asymmetric epoxidation;
DOI:10.1246/bcsj.78.1549