(1S,2R,6S,11aS,13S,14aR)-1,13-dihydroxy-2-[(2-hydroxyethyl)sulfanyl]-6-methyl-1,2,3,6,7,8,9,11a,12,13,14,14a-dodecahydro-4H-cyclopenta[f]oxacyclotridecin-4-one -Drug Synthesis Database

【结构式】

【分子编号】53115

【品名】(1S,2R,6S,11aS,13S,14aR)-1,13-dihydroxy-2-[(2-hydroxyethyl)sulfanyl]-6-methyl-1,2,3,6,7,8,9,11a,12,13,14,14a-dodecahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

【CA登记号】n/a

【分子式】C₁₈H₃₀O₅S

【分子量】358.4992

【元素组成】C 60.31% H 8.43% O 22.31% S 8.94%

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：(III)

Michael addition of 2-mercaptoethanol (II) to the unsaturated lactone function of (+)-brefeldin A (I) in the presence of Proton Sponge afforded the sulfanyl adduct (III). The title sulfoxide was then obtained by oxidation of sulfide (III) with meta-chloroperbenzoic acid.

参考文献中间体

合成目标

【1】 Fox, B.M.; et al.; Design and synthesis of (+)-brefeldin A sulfide prodrugs with enhanced aqueous solubilities. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 97.
【2】 Argade, A.B.; Devraj, R.; Vroman, J.A.; Haugwitz, R.D.; Hollingshead, M.; Cushman, M.; Design and synthesis of brefeldin A sulfide derivatives as prodrug candidates with enhanced aqueous solubilities. J Med Chem 1998, 41, 18, 3337.
【3】 Cushman, M.S.; Devraj, R.; Argade, A.B.; Haughwitz, R.D. (Purdue Research Foundation); Brefeldin A derivs.. US 6362218; WO 9931084 .

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)	53114	(1S,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one	n/a	C₁₆H₂₄O₄	详情	详情
(II)	36375	2-Sulfanyl-1-ethanol; 2-Mercaptoethanol	60-24-2	C₂H₆OS	详情	详情
(III)	53115	(1S,2R,6S,11aS,13S,14aR)-1,13-dihydroxy-2-[(2-hydroxyethyl)sulfanyl]-6-methyl-1,2,3,6,7,8,9,11a,12,13,14,14a-dodecahydro-4H-cyclopenta[f]oxacyclotridecin-4-one	n/a	C₁₈H₃₀O₅S	详情	详情

Extended Information