(4S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane -Drug Synthesis Database

【结构式】

【分子编号】45778

【品名】(4S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane

【CA登记号】60456-22-6

【分子式】C₆H₁₁ClO₂

【分子量】150.60484

【元素组成】C 47.85% H 7.36% Cl 23.54% O 21.25%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

Reaction of 3-(4-hydroxyphenyl)propionic acid (I) with the chiral dioxolanylmethyl chloride (II) afforded the corresponding dioxolanylmethyl ester (III). The phenolic hydroxyl group of (III) was then alkylated with (S)-bromohydrin (IV) to produce the intermediate (V).

参考文献中间体

合成目标

【1】 Iguchi, S.; Kawamura, M.; Miyamoto, T. (Ono Pharmaceutical Co., Ltd.); Novel esters of phenylalkanoic acid. EP 0397031; JP 1991072475; JP 1994073044; US 5013734 .

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)	25691	3-(4-hydroxyphenyl)propionic acid	501-97-3	C₉H₁₀O₃	详情	详情
(II)	45778	(4S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane	60456-22-6	C₆H₁₁ClO₂	详情	详情
(III)	48332	[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-(4-hydroxyphenyl)propanoate		C₁₅H₂₀O₅	详情	详情
(IV)	48333	(2S)-2-(bromomethyl)oxirane		C₃H₅BrO	详情	详情
(V)	48334	[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)oxiranylmethoxy]phenyl]propanoate		C₁₈H₂₄O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Alkylation of N-ethyl p-toluenesulfonamide (I) with (S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (II) afforded the N,N-dialkylated tosylamide (III). Deprotection of ketal (III), followed by selective mono tosylation of the resulting diol (IV), yielded (V), which was cyclized to epoxide (VI) upon treatment with K2CO3 in MeOH. Epoxide ring opening with N,N'-dibenzyl-1,3-diaminopropane (VII) gave the fully protected tetraamine (VIII). Removal of the p-toluenesulfonyl groups of (VIII) was accomplished using sodium naphthalenide providing (IX). Finally, hydrogenolytic debenzylation of (IX) furnished the title tetraamine.

参考文献中间体

合成目标

【1】 McManis, J.S.; Smith, R.E.; Weimar, W.R.; Muller, R.; Merriman, R.L.; Bussenieus, J.; Yao, H.; Bergeron, R.J.; Synthesis and evaluation of hydroxylated polyamine analogues as antiproliferatives. J Med Chem 2000, 43, 2, 224.

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)	45777	N-ethyl-4-methylbenzenesulfonamide	80-39-7	C₉H₁₃NO₂S	详情	详情
(II)	45778	(4S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane	60456-22-6	C₆H₁₁ClO₂	详情	详情
(III)	45779	N-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-N-ethyl-4-methylbenzenesulfonamide		C₁₅H₂₃NO₄S	详情	详情
(IV)	45780	N-[(2R)-2,3-dihydroxypropyl]-N-ethyl-4-methylbenzenesulfonamide		C₁₂H₁₉NO₄S	详情	详情
(V)	45781	(2R)-3-[ethyl[(4-methylphenyl)sulfonyl]amino]-2-hydroxypropyl 4-methylbenzenesulfonate		C₁₉H₂₅NO₆S₂	详情	详情
(VI)	45782	N-ethyl-4-methyl-N-[(2R)oxiranylmethyl]benzenesulfonamide		C₁₂H₁₇NO₃S	详情	详情
(VII)	45783	N-benzyl-N-[3-(benzylamino)propyl]amine; N(1),N(3)-dibenzyl-1,3-propanediamine		C₁₇H₂₂N₂	详情	详情
(VIII)	45784	N-[(2S)-3-(benzyl[3-[benzyl((2S)-3-[ethyl[(4-methylphenyl)sulfonyl]amino]-2-hydroxypropyl)amino]propyl]amino)-2-hydroxypropyl]-N-ethyl-4-methylbenzenesulfonamide		C₄₁H₅₆N₄O₆S₂	详情	详情
(IX)	45785	(5R,13R)-7,11-dibenzyl-3,7,11,15-tetraazaheptadecane-5,13-diol		C₂₇H₄₄N₄O₂	详情	详情

Extended Information