(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one -Drug Synthesis Database

【结构式】

【分子编号】59382

【品名】(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one

【CA登记号】

【分子式】C₂₀H₂₈O₆

【分子量】364.43872

【元素组成】C 65.92% H 7.74% O 26.34%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(I)

The acylation of phorbol (I) with tetradecanoyl chloride (II) in pyridine gives the triacyl phorbol (III), which is selective hydrolyzed with NaOMe in methanol at room temperature to yield the monoacyl phorbol (IV). The acylation of (IV) with acetic anhydride in pyridine at 8 C affords the diacetoxy tetradecanoyloxy phorbol (V). Finally, this compound is monodeacetylated by means of HClO4 in methanol at room temperature to provide the target mixed diacylphorbol.

参考文献中间体

合成目标

【1】 Bresch, H.; et al.; Active components of croton oil. IX. Partial synthesis of the active components of croton oil. Z Naturforsch B - J Chem Sci 1968, 23, 4, 539.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	59382	(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one		C₂₀H₂₈O₆	详情	详情
(II)	30295	tetradecanoyl chloride	112-64-1	C₁₄H₂₇ClO	详情	详情
(III)	59383	[(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-9,9a-bis(tetradecanoyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-3-yl]methyl myristate		C₆₂H₁₀₆O₉	详情	详情
(IV)	59384	(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9a-trihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate		C₃₄H₅₄O₇	详情	详情
(V)	59385	(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-3-[(acetyloxy)methyl]-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate		C₃₈H₅₈O₉	详情	详情

Extended Information