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【结 构 式】

【分子编号】32132

【品名】([1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]methyl)(triphenyl)phosphonium chloride

【CA登记号】

【 分 子 式 】C28H28ClN2O6P

【 分 子 量 】554.966662

【元素组成】C 60.6% H 5.09% Cl 6.39% N 5.05% O 17.3% P 5.58%

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:(III)

Treatment of 5-hydroxymethyl-1-beta-D-arabinofuranosyluracil (I) with hydrogen chloride in dioxane affords the 5-chloromethyl derivative (II), which is converted to the triphenylphosphonium salt (III). The Wittig reaction of (III) by means of paraformaldehyde and n-butyllithium in DMF yields the 5-vinyl derivative (IV), and bromination of (IV) with bromine in DMF under a heated condition affords BVAU.

1 Senda, S.; Mizuno, Y.; Shibuya, S.; Ikeda, K.; Sakata, S.; Machida, H.; Hirota, K.; Yoshino, H.; Synthesis and antiherpes-viral activity of 5-C-substituted uracil nucleosides. Nucleic Acids Res Symp Ser 1980, 8, 8, S39-S42.
2 Sakata, S.; Machida, H.; BVAU. Drugs Fut 1982, 7, 7, 458.
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) 32130 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-(hydroxymethyl)-2,4(1H,3H)-pyrimidinedione; 5-hydroxymethyl-1-beta-D-arabinofuranosyluracil C10H14N2O7 详情 详情
(II) 32131 5-(chloromethyl)-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione C10H13ClN2O6 详情 详情
(III) 32132 ([1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]methyl)(triphenyl)phosphonium chloride C28H28ClN2O6P 详情 详情
(IV) 32133 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-vinyl-2,4(1H,3H)-pyrimidinedione C11H14N2O6 详情 详情
Extended Information