methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14Z-trienoate

Base Information Edit

Chemical Name:methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14Z-trienoate
CAS No.:75879-51-5
Molecular Formula:C₄₀H₅₈O₅Si
Molecular Weight:646.983
Hs Code.:
Mol file:75879-51-5.mol

Synonyms:methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14Z-trienoate

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Chemical Property of methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14Z-trienoate Edit

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Technology Process of methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14Z-trienoate

There total 31 articles about methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14Z-trienoate 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: 80.0%

: 4762-26-9
hexyltriphenylphosphonium bromide

: 75879-50-4
methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-14-oxo-tetradeca-5Z,12E-dienoate

: 75879-51-5
methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14Z-trienoate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; 1.) -78 deg C, 2.) to room temperature;

Reference yield: 70.0%

: 4762-26-9
hexyltriphenylphosphonium bromide

: 75646-92-3
methyl 8R-tert-butyldiphenylsilyloxy-9R,11R-dihydroxy-9,11-O-isopropylidene-14-oxo-tetradeca-5Z,12E-dienoate

: 75646-93-4,75879-51-5
methyl 8R-tert-butyldimethylsilyloxy-9R,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14-trienoate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; 1.) room temperature, 10 min, 2.) -78 deg C;

Reference yield:

: 2946-01-2
(3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate

: 75646-93-4,75879-51-5
methyl 8R-tert-butyldimethylsilyloxy-9R,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14-trienoate

Guidance literature:: Multi-step reaction with 13 steps

1: p-toluenesulfonic acid / 0.5 h / Heating

2: 65 percent / soda lime / benzene / 225 - 235 °C / 5 Torr

3: hydrogen / 5 percent Pd/C / ethyl acetate / 0.17 h

4: 1.) p-toluenesulfonyl chloride, pyridine, 2.) 1 N KOH / 1.) CH₂Cl₂, 0 deg C, 3 h; room temperature, 20 h, 2.) MeOH/H₂O, 0 deg C

5: 1.) n-BuLi / hexamethylphosphoric acid triamide; hexane / 1.) 5 deg C, 2.) room temperature, 20 h

6: diethyl ether

7: hydrogen, ethylene diamine / nickel acetate, sodium borohydride / ethanol; H₂O

8: imidazole / dimethylformamide / 17 h / 78 °C

9: 85 percent / zinc chloride / 1 h / -10 °C

10: p-toluenesulfonic acid / acetone / 0.25 h / Ambient temperature

11: 75 percent / mercuric oxide, mercuric chloride / acetone; H₂O / 6 h / Ambient temperature

12: 70 percent / dimethylformamide / 20 h / Ambient temperature

13: 70 percent / 1.) n-BuLi / tetrahydrofuran / 1.) room temperature, 10 min, 2.) -78 deg C

With pyridine; 1H-imidazole; potassium hydroxide; n-butyllithium; soda lime; hydrogen; toluene-4-sulfonic acid; ethylenediamine; p-toluenesulfonyl chloride; mercury dichloride; mercury(II) oxide; zinc(II) chloride; sodium tetrahydroborate; palladium on activated charcoal; nickel diacetate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;