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【结 构 式】

【分子编号】41892

【品名】1,1-dimethoxycyclopentane; 1-methoxycyclopentyl methyl ether

【CA登记号】931-94-2

【 分 子 式 】C7H14O2

【 分 子 量 】130.18696

【元素组成】C 64.58% H 10.84% O 24.58%

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:(II)

The reaction of 5-methyluridine (I) with 1,1-dimethoxycyclopentane (II) by means of TsOH in hot dichloroethane gives the corresponding cyclic ketal (III), which is protected with 4-methoxybenzyl bromide and NaH in DME yielding the N,O-diprotected compound (IV). Elimination of the ketal protecting group of (IV) with dichloroacetic acid in water affords N3,O5'-bis(4-methoxybenzyl)-5-methyluridine (V), which is treated with PPh3, I2 and imidazole in hot toluene/acetonitrile to provide 2',3'-didehydro-2',3'-dideoxy-N3,O5’-bis(4-methoxybenzyl)-5-methyluridine (VI). Finally this compound is deprotected with ammonium cerium (IV) nitrate in acetonitrile/water.

1 Luzzio, F.A.; Menes, M.E.; A facile route to pyrimidine-based nuceloside olefins: Application to the synthesis of d4T(stavudine). J Org Chem 1994, 59, 24, 7267.
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) 12206 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine 1463-10-1 C10H14N2O6 详情 详情
(II) 41892 1,1-dimethoxycyclopentane; 1-methoxycyclopentyl methyl ether 931-94-2 C7H14O2 详情 详情
(III) 41893   C15H20N2O6 详情 详情
(IV) 41894   C31H36N2O7 详情 详情
(V) 41895 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(4-methoxyphenethyl)tetrahydro-2-furanyl]-3-(4-methoxybenzyl)-5-methyl-2,4(1H,3H)-pyrimidinedione C26H30N2O7 详情 详情
(VI) 41896 3-(4-methoxybenzyl)-1-[(2R,5R)-5-(4-methoxyphenethyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione C26H28N2O5 详情 详情
Extended Information