wybutine | 35693-91-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: wybutine
• 英文别名: methyl (2S)-4-(4,6-dimethyl-9-oxo-1H-imidazo[1,2-a]purin-7-yl)-2-(methoxycarbonylamino)butanoate
• CAS: 35693-91-5
• 化学式: C₁₆H₂₀N₆O₅
• 分子量: 376.372
• InChiKey: ILBRXFOKTSWVQE-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl (2S)-2-[5-(1-benzyl-4,6-dimethyl-9-oxoimidazo[1,2-a]purin-7-yl)-2-oxo-1,3-dioxolan-4-yl]-2-(methoxycarbonylamino)acetate 生成 wybutine
  参考文献：
  名称：

  ITAYA, TAISUKE;WATANABE, NOBUHIDE;MIZUTANI, AKEMI, 14TH SYMP. NUCL. ACIDS CHEM., TOKUSHIMA, OCT. 30TH - NOV. 1ST, 1986, OXFO+

  摘要：

  DOI：

文献信息

• Synthesis and Absolute Configuration of Wybutine, the Fluorescent Minor Base from Phenylalanine Transfer Ribonucleic Acids.
  作者：Taisuke ITAYA、Akemi MIZUTANI、Takehiko IIDA

  DOI：10.1248/cpb.39.1407

  日期：——

  The phosphonium chloride 6 having an optically active amino acid moiety was synthesized from (S)-serine benzylester tosylate (2b) through a six-step route. The utility of 6 as a reagent for the Witting reaction was exemplified in the olefination with benzaldehyde, affording the (E)-β, γ-unsaturated amino acid derivative 11 as a sole geometrical ispmer. This new method of amino acid homologation was successuflly employed for the first chiral synthesis of wybutine (1c), the minor base isolated from yeast phenylalanine transfer ribonucleic acids : the Wittig reaction between 6 and the tricyclic aldehyde 16 followed successively by methylation and catalytic reduction afforded 1c. Comparison of wybutine with synthetic 1c has unequivocally established that wybutine has an S configuration.

  含有光学活性氨基酸部分的氯化膦 6 是通过一条六步合成路线从 (S)-丝氨酸苄酯对甲苯磺酸酯 (2b) 合成的。6 作为 Witting反应试剂的实用性在苯甲醛的烯化反应中得到了体现, 得到了唯一的 (E)-β, γ-不饱和氨基酸衍生物 11。这种新的氨基酸同系化方法成功地应用于黄曲霉素 (1c)的首次手性合成, 黄曲霉素是从酵母苯丙氨酸转移核糖核酸中分离得到的次要碱基。6 与三环醛 16 的 Wittig 反应之后接着进行甲基化和催化还原,从而得到了 1c。黄曲霉素与合成物 1c 的比较明确地证明了黄曲霉素具有 S 构型。
• Synthesis of (S-(−)-wybutine, the fluorescent minor base from yeast phenylalanine transfer ribonucleic acids
  作者：Taisuke Itaya、Akemi Mizutani

  DOI：10.1016/s0040-4039(01)80814-5

  日期：——

  The Wittig reaction of 1-benzyl-7-formylwye (12) with (R)-[2-carboxy-2-[(methoxycarbonyl)amino]ethyl]triphenylphosphonium chloride (8) followed by successive methylation and reduction gave (-)-wybutine [(S)-1a].

  1-苄基-7-甲酰基wye（12）与（R）-[2-羧基-2-[（甲氧羰基氨基）乙基]三苯基phosph氯化物（8）的Wittig反应，接着连续甲基化和还原得到（-）- wybutine [（小号） - 1A ]。
• Access to the synthesis of wybutosine, the first tricyclic fluorescent nucleoside isolated from phenyllalanine transfer ribonucleic acids
  作者：Taisuke Itaya、Manabu Shimomichi、Masako Ozasa

  DOI：10.1016/s0040-4039(00)80435-9

  日期：1988.1

  An improved synthesis of the key intermediate 5 for the chiral syntheses of wybutine (1c) and hydroxywybutine (1d) has been achieved by palladium-catalyzed vinylation, which has been utilized for the first synthesis of 3-β-D-ribofuranosylwybutine (2c).

  关键中间体的改进的合成5为wybutine（的手性合成1C）和hydroxywybutine（1D）已经由钯催化的乙烯化，其已用于3-β-d-ribofuranosylwybutine（第一合成实现图2c） 。
• Synthesis of optically active forms of hydroxy-y base, the minor component of rat liver phenylalanine transfer ribonucleic acid
  作者：Taisuke Itaya、Nobuhide Watanabe、Akemi Mizutani

  DOI：10.1016/s0040-4039(00)84906-0

  日期：——

  [R-(R*,S*)]-e-Hydroxywybutine (6) and its [S-(R*,S*)]-isomer (9) have been synthesized as the most probable alternatives for hydroxy-Y base isolated from rat liver phenylalanine tRNA.

  [ R-（R *，S *）]-e-羟基维丁汀（6）及其[ S-（R *，S *）]-异构体（9）已被合成为分离的羟基Y碱的最可能替代品来自大鼠肝脏的苯丙氨酸tRNA。
• Synthesis of β-hydroxywybutines, the most probable alternatives for the hypermodified base of rat liver phenylalanine transfer ribonucleic acid
  作者：Taisuke Itaya、Nobuhide Watanabe、Takehiko Iida、Tae Kanai、Akemi Mizutani

  DOI：10.1016/0040-4020(95)00302-o

  日期：1995.6

  Deoxygenation of the 1,2-glycol (±)-5 was achieved at the position adjacent to the heterocycle through the cyclic carbonate (±)-14, providing the monohydroxy compound 6. This new method of regioselective deoxygenation was employed for the first synthesis of β-hydroxywybutines : oxidation of the methyl butenoate 7 with osmium tetroxide, followed by deoxygenation through the cyclic carbonates (19 and

  在与杂环通过环状碳酸酯（±）-14相邻的位置上实现了1,2-乙二醇（±）-5的脱氧，得到了单羟基化合物6。这种新的区域选择性脱氧方法被用于β-羟基丁酮的首次合成：用四氧化氧化丁烯酸甲酯7，然后通过环状碳酸酯（19和20）脱氧，得到2的两个非对映异构体。