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【结 构 式】

【分子编号】61198

【品名】(2S)-2-hydroxycyclopentanone

【CA登记号】

【 分 子 式 】C5H8O2

【 分 子 量 】100.11732

【元素组成】C 59.98% H 8.05% O 31.96%

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 synthesis of the 1,3-dioxane intermediate (XIII) has been performed as follows: The reaction of 2(S)-hydroxycyclopentanone (I) with Tbdps-Cl and imidazole in DMF gives the silyl ether (II), which is condensed with the phosphonate (III) by means of BuLi in THF to yield the new phosphonate (IV) after silylation with Tes-Cl and LDA. The Horner-Wadsworth-Emmons olefination of carbaldehyde (V) with phosphonate (IV) by means of LiCl and TEA in THF affords the silylated ketone (VI), which is reduced with NaBH4/CeCl3 and protected with Mom-Cl and DIEA to provide the dihydropyran derivative (VII). The cleavage of the Tes protecting group by means of TsOH, followed by oxidation of the resulting alcohol with SO3/pyridine in DMSO/dichloromethane gives the aldehyde (VIII). A new olefination reaction of aldehyde (VIII) with phosphorane (IX) by means of NaH in THF yields the methoxyamide (X), which is reduced with DIBAL in THF to afford the unsaturated aldehyde (XI). Finally, this aldehyde is treated with (2R,4R)-pentanediol (XII) and montmorillonite K-10 in hot toluene to provide the target 1,3-dioxane intermediate (XIII).

1 Mulzer, J.; Hanbauer, M.; Total synthesis of the antitumor agent (-)-laulimalide. Tetrahedron Lett 2002, 43, 18, 3381.
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) 61198 (2S)-2-hydroxycyclopentanone C5H8O2 详情 详情
(II) 61199 (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}cyclopentanone C21H26O2Si 详情 详情
(III) 61200 dipropyl methylphosphonate C7H17O3P 详情 详情
(IV) 61201 dipropyl (3S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-oxo-5-[(triethylsilyl)oxy]pentylphosphonate C33H55O6PSi2 详情 详情
(V) 61148 (2S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde C7H10O2 详情 详情
(VI) 61202 (E,4S)-4-{[tert-butyl(diphenyl)silyl]oxy}-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-[(triethylsilyl)oxy]-1-hexen-3-one C34H50O4Si2 详情 详情
(VII) 61203 (5S,6S)-6-{[tert-butyl(diphenyl)silyl]oxy}-10,10-diethyl-5-{(E)-2-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]ethenyl}-2,4,9-trioxa-10-siladodecane; tert-butyl(diphenyl)silyl (1S,2S,3E)-2-(methoxymethoxy)-4-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-1-{2-[(triethylsilyl)oxy]ethyl}-3-butenyl ether C36H56O5Si2 详情 详情
(VIII) 61204 (3S,4S,5E)-3-{[tert-butyl(diphenyl)silyl]oxy}-4-(methoxymethoxy)-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-5-hexenal C30H40O5Si 详情 详情
(IX) 61205 dipropyl 2-[methoxy(methyl)amino]-2-oxoethylphosphonate C10H22NO5P 详情 详情
(X) 61206 (2E,5S,6S,7E)-5-{[tert-butyl(diphenyl)silyl]oxy}-N-methoxy-6-(methoxymethoxy)-N-methyl-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-2,7-octadienamide C34H47NO6Si 详情 详情
(XI) 61154 (2E,5S,6S,7E)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-2,7-octadienal C32H42O5Si 详情 详情
(XII) 57935 (2S,4S)-2,4-pentanediol C5H12O2 详情 详情
(XIII) 61155 tert-butyl(diphenyl)silyl (1S,2S,3E)-1-{(E)-3-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]-2-propenyl}-2-(methoxymethoxy)-4-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-3-butenyl ether; (5S,6S)-6-{(E)-3-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]-2-propenyl}-9,9-dimethyl-5-{(E)-2-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]ethenyl}-8,8-diphenyl-2,4,7-trioxa-8-siladecane C37H52O6Si 详情 详情
Extended Information