(2S)-2-isopropyloxirane -Drug Synthesis Database

【结构式】

【分子编号】53771

【品名】(2S)-2-isopropyloxirane

【CA登记号】123731-68-0

【分子式】C₅H₁₀O

【分子量】86.1338

【元素组成】C 69.72% H 11.7% O 18.58%

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：(XCIII)

Diazotization of (S)-valine (LXXXIX) gave rise to the alpha-hydroxyacid (XC), which was reduced to diol (XCI) using LiAlH4. Tosylation of the primary hydroxyl of (XCI), followed by cyclization of the resulting tosylate (XCII) under basic conditions, furnished epoxide (XCIII). Condensation of epoxide (XCIII) with the lithium anion derived from sulfone (LXXXVIII) gave adduct (XCIV). Reductive elimination of the phenylsulfonyl group and then acidic rearrangement of the cyclopropane ring provided the dihydroxy steroid (XCV). After protection of (XCV) as the diacetate (XCVI), allylic oxidation with CrO3 in the presence of dimethylpyrazole yielded enone (XCVII).

参考文献中间体

合成目标

【1】 Moriarty, R.M.; et al.; Stereoselective synthesis of squalamine dessulfate. Tetrahedron Lett 1995, 36, 29, 5139.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(LXXXVII)	53768	(2S)-2-[(1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl]propyl phenyl sulfone; {(2S)-2-[(1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl]propyl}(dioxo)phenyl-lambda~6~-sulfane	n/a	C₂₉H₄₂O₃S	详情	详情
(LXXXIX)	37828	L-2-Amino-3-methylbutyric acid; L-2-Aminoisovaleric acid; 2-Aminoisovaleric acid; L-2-Amino-3-methylbutyric acid; L-alpha-Aminoisovaleric acid; L-valine; (S)-(+)-Valine; (S)-alpha-Aminoisovaleric acid	72-18-4	C₅H₁₁NO₂	详情	详情
(XC)	37829	(2S)-2-hydroxy-3-methylbutyric acid		C₅H₁₀O₃	详情	详情
(XCI)	53769	(2S)-3-methyl-1,2-butanediol	n/a	C₅H₁₂O₂	详情	详情
(XCII)	53770	(2S)-2-hydroxy-3-methylbutyl 4-methylbenzenesulfonate	n/a	C₁₂H₁₈O₄S	详情	详情
(XCIII)	53771	(2S)-2-isopropyloxirane	123731-68-0	C₅H₁₀O	详情	详情
(XCIV)	53772	(3R,6S)-6-[(1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl]-2-methyl-5-(phenylsulfonyl)-3-heptanol	n/a	C₃₄H₅₂O₄S	详情	详情
(XCV)	53773	(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol	n/a	C₂₇H₄₆O₂	详情	详情
(XCVI)	53774	(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate	n/a	C₃₁H₅₀O₄	详情	详情
(XCVII)	53775	(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethyl-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate		C₃₁H₄₈O₅	详情	详情

Extended Information