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【结 构 式】

【分子编号】53775

【品名】(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

【CA登记号】

【 分 子 式 】C31H48O5

【 分 子 量 】500.71912

【元素组成】C 74.36% H 9.66% O 15.98%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XCVII)

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).

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

合成路线2

该中间体在本合成路线中的序号:(XCVII)

Birch reduction of enone (XCVII), followed by reduction of the saturated ketone (XCVIII) with K-Selectride, provided alcohol (XCIX). Acetylation of (IC) gave the triacetate (C). Selective hydrolysis of the C-3 acetate group of (C) with NaCN in MeOH yielded alcohol (CI), which was oxidized to ketone (CII) by using the Jones reagent.

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
(IC) 53777 (3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate C31H52O5 详情 详情
(CI) 53779 (3S,5R,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate C31H52O5 详情 详情
(CII) 53780 (5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate C31H50O5 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
(XCVIII) 53776 (3S,5R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate C31H50O5 详情 详情
(C) 53778 (3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-(acetyloxy)-17-[(1R,4R)-4-(acetyloxy)-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate C33H54O6 详情 详情
Extended Information