Technology Process of (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis(tert-butyldimethylsilyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid
There total 1 articles about (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis(tert-butyldimethylsilyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid which
guide to synthetic route it.
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synthetic route:
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188730-19-0
(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis(tert-butyldimethylsilyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid
- Guidance literature:
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Multi-step reaction with 16 steps
1: 70 percent / DIBAL-H / CH2Cl2 / -78 °C
2: 90 percent / benzene / Heating
3: Bu3P(O); Et2AlCl; (S)-3,3'-(Ph2PO)2-1,1'-binaphthalene-2,2'-diol / CH2Cl2; hexane / 39 h / -40 °C
4: TFA / CH2Cl2; hexane / 1 h / 20 °C
5: 75 percent / H2SO4 / Heating
6: 99 percent / imidazole / dimethylformamide
7: 87 percent / DIBAL-H / toluene / -78 °C
8: tetrahydrofuran / -78 °C
9: tetrahydrofuran
10: 51 percent / HCO2NH4; Bu3P / Pd(OAc)2 / benzene / 50 °C
11: 89 percent / AcOH; H2O / tetrahydrofuran / 50 °C
12: 90 percent / [Ti(O-i-Pr)4]; i-PrMgCl / diethyl ether / -78 - -50 °C
13: 65 percent / I2 / CH2Cl2
14: 90 percent / NEt3; DMAP / CH2Cl2
15: 50 percent / 9-BBN; K3PO4 / [PdCl2(dppf)] / tetrahydrofuran; dimethylformamide; H2O / 60 °C
16: 84 percent / NaOH; H2O / methanol
With
1H-imidazole; titanium(IV) isopropylate; dmap; sodium hydroxide; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; tributylphosphine; Tributylphosphine oxide; sulfuric acid; water; iodine; isopropylmagnesium chloride; ammonium formate; diethylaluminium chloride; diisobutylaluminium hydride; acetic acid; triethylamine; trifluoroacetic acid; 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-bis-diphenylphosphine oxide;
palladium diacetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
1: Reduction / 2: Condensation / 3: Addition / 4: Acidolysis / 5: Addition / 6: Etherification / 7: Reduction / 8: Addition / 9: Esterification / 10: Reductive deoxygenation / 11: Hydrolysis / 12: Reduction / 13: Iodination / 14: Acetylation / 15: Suzuki coupling / 16: Hydrolysis;
DOI:10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F
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188730-19-0
(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis(tert-butyldimethylsilyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid
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2,4,6-Trichloro-benzoic acid (Z)-(1S,8S,9S,10R,13S)-9,13-bis-(tert-butyl-dimethyl-silanyloxy)-14-carboxy-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-11-oxo-tetradec-3-enyl ester
- Guidance literature:
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With
triethylamine;
In
tetrahydrofuran;
at 20 ℃;
for 0.25h;
DOI:10.1021/ja971946k
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188730-19-0
(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis(tert-butyldimethylsilyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid
- Guidance literature:
-
With
triethylamine;
In
tetrahydrofuran;
at 20 ℃;
for 0.833333h;
DOI:10.1002/chem.200305669
