ChemicalBook CAS DataBase List (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-TRIS-{[TERT-BUTYL(DIMETHYL)SILYL]OXY}-4,4,6,8,12,16-HEXAMETHYL-17-(2-METHYL-1,3-THIAZOL-4-YL)-5-OXO-HEPTADECA-12,16-DIENOIC ACID

(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-TRIS-{[TERT-BUTYL(DIMETHYL)SILYL]OXY}-4,4,6,8,12,16-HEXAMETHYL-17-(2-METHYL-1,3-THIAZOL-4-YL)-5-OXO-HEPTADECA-12,16-DIENOIC ACID synthesis

12synthesis methods

Product Name:(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-TRIS-{[TERT-BUTYL(DIMETHYL)SILYL]OXY}-4,4,6,8,12,16-HEXAMETHYL-17-(2-METHYL-1,3-THIAZOL-4-YL)-5-OXO-HEPTADECA-12,16-DIENOIC ACID
CAS Number:193146-63-3
Molecular formula:C45H85NO6SSi3
Molecular Weight:852.48

12,16-Heptadecadienal, 3,7,15-tris[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-4-thiazolyl)-5-oxo-, (3S,6R,7S,8S,12Z,15S,16E)-

193146-54-2
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(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-TRIS-{[TERT-BUTYL(DIMETHYL)SILYL]OXY}-4,4,6,8,12,16-HEXAMETHYL-17-(2-METHYL-1,3-THIAZOL-4-YL)-5-OXO-HEPTADECA-12,16-DIENOIC ACID

193146-63-3
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Yield:193146-63-3 4.4 g

Reaction Conditions:

with sodium chlorite;sodium dihydrogenphosphate dihydrate in water;tert-butyl alcohol at 0 - 30; for 2 h;

Steps:

41 Example-41: Preparation of (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-tris(tert- butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2methylthiazol-4-yl)-5- oxoheptadeca-12,16-dienoic acid (Formula D-Va)

Example-41: Preparation of (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-tris(tert- butyldimethylsilyloxy)-4,4,6,8,12,16-hexamethyl-17-(2methylthiazol-4-yl)-5- oxoheptadeca-12,16-dienoic acid (Formula D-Va) A mixture of (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-tris(tert-butyldimethylsilyloxy)- 4,4,6,8, 12,16-hexamethyl- 17-(2-methylthiazol-4-yl)-5-oxoheptadeca- 12, 16-dienal compound of formula D-IVa (4 gm), tert-butanol (150 ml) and water (40 ml) was cooled to 0-5°C and stirred for 10 min at the same temperature. 2-Methyl-2-butene (15.2 ml), 80% sodium chlorite (1.72 gm) and sodium dihydrogen phosphate dihydrate (1.5 gm) were added to the reaction mixture at 0-5°C. Raised the temperature of the reaction mixture to 25-30°C and stirred for 2 hrs at the same temperature. Both the organic and aqueous layers were separated and distilled off the organic layer under reduced pressure. Ethyl acetate and aqueous sodium chloride solution were added to the obtained residue and stirred for 15 min. Both the organic and aqueous layers were separated and distilled off the solvent completely from the organic layer under reduced pressure to get the title compound. Yield: 4.4 gm.

References:

WO2015/87351,2015,A2 Location in patent:Page/Page column 56-57

193146-53-1 Synthesis