(2S)-2-hydroxypropyl 4-methylbenzenesulfonate -Drug Synthesis Database

【结构式】

【分子编号】53385

【品名】(2S)-2-hydroxypropyl 4-methylbenzenesulfonate

【CA登记号】n/a

【分子式】C₁₀H₁₄O₄S

【分子量】230.28476

【元素组成】C 52.16% H 6.13% O 27.79% S 13.92%

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：(IV)

A stereoselective synthesis for the title 2'S isomer was also reported, employing (S)-1-mercapto-2-propanol (VII). Conversion of the chiral tosylate (IV) to the trityl sulfide (V) was achieved by treatment with the lithium thiolate of triphenylmethanethiol. The trityl group of (V) was then removed by iodine in MeOH, producing disulfide (VI). This was reduced with NaBH4 to the corresponding thiol (VII), which was subsequently added to brefeldin A (I), producing the desired sulfide isomer (VIII). Final oxidation of sulfide (VIII) with m-CPBA yielded the target sulfoxide.

参考文献中间体

合成目标

【1】 Fox, B.M.; et al.; Preparation and evaluation of sulfide derivatives of the antibiotic brefeldin A as potential prodrug candidates with enhanced aqueous solubilities. J Med Chem 2001, 44, 23, 3915.

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)	53314	acetone O-benzyloxime	n/a	C₁₀H₁₃NO	详情	详情
(IV)	53385	(2S)-2-hydroxypropyl 4-methylbenzenesulfonate	n/a	C₁₀H₁₄O₄S	详情	详情
(V)	53386	(2S)-1-(tritylsulfanyl)-2-propanol	n/a	C₂₂H₂₂OS	详情	详情
(VI)	53387	(2S)-1-{[(2S)-2-hydroxypropyl]disulfanyl}-2-propanol	n/a	C₆H₁₄O₂S₂	详情	详情
(VII)	53388	(2S)-1-sulfanyl-2-propanol	n/a	C₃H₈OS	详情	详情
(VIII)	53383	(1S,2R,6S,11aS,13S)-1,13-dihydroxy-2-{[(2S)-2-hydroxypropyl]sulfanyl}-6-methyl-1,2,3,6,7,8,9,11a,12,13,14,14a-dodecahydro-4H-cyclopenta[f]oxacyclotridecin-4-one	n/a	C₁₉H₃₂O₅S	详情	详情

Extended Information