methyl 11R-acetoxy-8R-tert-butyldiphenylsilyloxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate

Base Information

Chemical Name:methyl 11R-acetoxy-8R-tert-butyldiphenylsilyloxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate
CAS No.:80126-59-6
Molecular Formula:C₃₉H₅₄O₇Si
Molecular Weight:662.939
Hs Code.:

Synonyms:methyl 11R-acetoxy-8R-tert-butyldiphenylsilyloxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate

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Chemical Property of methyl 11R-acetoxy-8R-tert-butyldiphenylsilyloxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate

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Technology Process of methyl 11R-acetoxy-8R-tert-butyldiphenylsilyloxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate

There total 10 articles about methyl 11R-acetoxy-8R-tert-butyldiphenylsilyloxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate 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: 90.0%

: 108-24-7
acetic anhydride

: 80126-58-5
methyl 8R-tert-butyldiphenylsilyloxy-11R-hydroxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate

: 80126-59-6
methyl 11R-acetoxy-8R-tert-butyldiphenylsilyloxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate

Guidance literature:: With dmap; triethylamine; In diethyl ether; for 0.5h; Ambient temperature;
DOI:10.1139/v81-394

Reference yield:

: 74581-59-2
methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-12-oxo-dodeca-5Z-enoate

: 80126-59-6
methyl 11R-acetoxy-8R-tert-butyldiphenylsilyloxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / diisopropylamine / dimethylformamide / Ambient temperature

2: triethylamine, 4-dimethylaminopyridine / diethyl ether / 0.5 h / Ambient temperature

3: 95 percent / K₂CO₃, dicyclohexyl-18-crown-6 / benzene / 6 h / 75 °C

4: 60 percent / 2N HCl / H₂O; methanol / 2 h / Ambient temperature

5: 80 percent / p-toluenesulfonic acid / acetone / Ambient temperature

6: 85 percent / triethylamine / CHCl₃ / Ambient temperature

7: 90 percent / triethylamine, 4-dimethylaminopyridine / diethyl ether / 0.5 h / Ambient temperature

With hydrogenchloride; dmap; perhydrodibenzo-18-crown-6; potassium carbonate; toluene-4-sulfonic acid; triethylamine; diisopropylamine; In methanol; diethyl ether; chloroform; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1139/v81-394

Reference yield:

: 74581-60-5
1-nitro-octan-3-one ethylene ketal

: 80126-59-6
methyl 11R-acetoxy-8R-tert-butyldiphenylsilyloxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / diisopropylamine / dimethylformamide / Ambient temperature

2: triethylamine, 4-dimethylaminopyridine / diethyl ether / 0.5 h / Ambient temperature

3: 95 percent / K₂CO₃, dicyclohexyl-18-crown-6 / benzene / 6 h / 75 °C

4: 60 percent / 2N HCl / H₂O; methanol / 2 h / Ambient temperature

5: 80 percent / p-toluenesulfonic acid / acetone / Ambient temperature

6: 85 percent / triethylamine / CHCl₃ / Ambient temperature

7: 90 percent / triethylamine, 4-dimethylaminopyridine / diethyl ether / 0.5 h / Ambient temperature

With hydrogenchloride; dmap; perhydrodibenzo-18-crown-6; potassium carbonate; toluene-4-sulfonic acid; triethylamine; diisopropylamine; In methanol; diethyl ether; chloroform; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1139/v81-394