(1S)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1-(3,3-diethoxyprop-1-ynyl)-1,4-imino-2,3-O-isopropylidene-D-ribitol | 488855-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1-(3,3-diethoxyprop-1-ynyl)-1,4-imino-2,3-O-isopropylidene-D-ribitol
• 英文别名: [(3aS,4S,6R,6aR)-4-(3,3-diethoxyprop-1-ynyl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-6-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 488855-75-0
• 化学式: C₂₁H₃₉NO₅Si
• 分子量: 413.63
• InChiKey: DSWHXNAAIYSPJC-OGWHTMIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1-(3,3-diethoxyprop-1-ynyl)-1,4-imino-2,3-O-isopropylidene-D-ribitol 在 吡啶 、 硝酸铵 、 盐酸 、 二氮烯 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 38.08h， 生成 (1S)-2,3,5,-tri-O-acetyl-1-(5-cyano-4-nitro-1H-pyrazol-3-yl)-1,4-dideoxy-1,4-imino-N-(2,2,2,-trichloroethoxycarbonyl)-D-ribitol
  参考文献：
  名称：

  8-Aza-immucillins as Transition-State Analogue Inhibitors of Purine Nucleoside Phosphorylase and Nucleoside Hydrolases

  摘要：

  The 8-aza-immucillins (8-aza-9-deazapurines linked from C9 to C1 of 1,4-dideoxy-1,4-iminoribitol) have been designed as transition-state analogues of the reactions catalyzed by purine nucleoside phosphorylase and nucleoside hydrolases. Syntheses of the 8-aza-immucillin analogues of inosine and adenosine are described. They are powerful inhibitors of the target enzymes with equilibrium dissociation constants as low as 42 pM.

  DOI：

  10.1021/jm0203332
• 作为产物：
  描述：

  4H-1,3-Dioxolo[4,5-c]pyrrole, 5-chloro-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-, (3aR,4R,6aS)- 在 正丁基锂 、 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 70.25h， 生成 (1S)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1-(3,3-diethoxyprop-1-ynyl)-1,4-imino-2,3-O-isopropylidene-D-ribitol
  参考文献：
  名称：

  8-Aza-immucillins as Transition-State Analogue Inhibitors of Purine Nucleoside Phosphorylase and Nucleoside Hydrolases

  摘要：

  The 8-aza-immucillins (8-aza-9-deazapurines linked from C9 to C1 of 1,4-dideoxy-1,4-iminoribitol) have been designed as transition-state analogues of the reactions catalyzed by purine nucleoside phosphorylase and nucleoside hydrolases. Syntheses of the 8-aza-immucillin analogues of inosine and adenosine are described. They are powerful inhibitors of the target enzymes with equilibrium dissociation constants as low as 42 pM.

  DOI：

  10.1021/jm0203332

文献信息

• Imino-<i>C</i>-nucleoside Synthesis:  Heteroaryl Lithium Carbanion Additions to a Carbohydrate Cyclic Imine and Nitrone
  作者：Gary B. Evans、Richard H. Furneaux、Herwig Hausler、Janus S. Larsen、Peter C. Tyler

  DOI：10.1021/jo035744k

  日期：2004.3.1

  Promotion by Lewis acid of the addition of some aryllithiums to a carbohydrate-based imine, which has allowed a more facile synthesis of some imino-C-nucleoside analogues, is described. Use of the corresponding nitrone does not assist in some cases, but lithiated acetonitrile adds to it efficiently to give a product from which further C-nucleoside analogues can be derived.

  促进通过加入一些芳基锂的一种基于碳水化合物的亚胺，其中已经允许的一些亚氨基的更容易合成的路易斯酸Ç核苷类似物，进行说明。在某些情况下，使用相应的腈没有帮助，但是将锂化的乙腈有效地添加到其中，可以得到可以进一步衍生出C-核苷类似物的产物。
• 8-Aza-immucillins as Transition-State Analogue Inhibitors of Purine Nucleoside Phosphorylase and Nucleoside Hydrolases
  作者：Gary B. Evans、Richard H. Furneaux、Graeme J. Gainsford、John C. Hanson、Gregory A. Kicska、Antony A. Sauve、Vern L. Schramm、Peter C. Tyler

  DOI：10.1021/jm0203332

  日期：2003.1.1

  The 8-aza-immucillins (8-aza-9-deazapurines linked from C9 to C1 of 1,4-dideoxy-1,4-iminoribitol) have been designed as transition-state analogues of the reactions catalyzed by purine nucleoside phosphorylase and nucleoside hydrolases. Syntheses of the 8-aza-immucillin analogues of inosine and adenosine are described. They are powerful inhibitors of the target enzymes with equilibrium dissociation constants as low as 42 pM.