2'-(O-tert-butyldimethylsilyl)-3'-α-(N-benzyl methylenesulfonamido)-3'-deoxy-uridine | 808148-15-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2'-(O-tert-butyldimethylsilyl)-3'-α-(N-benzyl methylenesulfonamido)-3'-deoxy-uridine
• 英文别名: N-benzyl-1-[(2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]methanesulfonamide
• CAS: 808148-15-4
• 化学式: C₂₃H₃₅N₃O₇SSi
• 分子量: 525.698
• InChiKey: KHMCSEVMKBBWJK-VURPSTOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-(O-tert-butyldimethylsilyl)-3'-α-(N-benzyl methylenesulfonamido)-3'-deoxy-uridine 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 生成 2'-(O-tert-butyldimethylsilyl)-3'-α-(methylenesulfonamido)-3'-deoxy-uridine
  参考文献：
  名称：

  A reversible safety-catch method for the hydrogenolysis of N-benzyl moieties

  摘要：

  The benzyl groups of beta-hydroxy-N-benzyl sulfonamides are labile toward hydrogenolysis-unlike N-benzyl sulfonamides lacking the beta-hydroxy moiety. We find that N-acyl-N-benzyl sulfonamides undergo hydrogenolysis under very mild conditions. Based upon these observations, we developed a reversible safety-catch method using tert-butoxycarbonyl moieties to activate N-benzyl sulfonamides toward hydrogenolysis. We also explored the utility of the safety-catch activation method for other nitrogen-based functionality such as N-benzyl carboxamides, imides, and related functionality. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.118
• 作为产物：
  描述：

  N-苄基甲烷磺酰胺 在 sodium tetrahydroborate 、 正丁基锂 、 thionyl diimidazole 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 21.5h， 生成 2'-(O-tert-butyldimethylsilyl)-3'-α-(N-benzyl methylenesulfonamido)-3'-deoxy-uridine
  参考文献：
  名称：

  Johnson II, David C.; Widlanski, Theodore S., Synthesis, 2002, # 6, p. 809 - 815

  摘要：

  DOI：

文献信息

• A reversible safety-catch method for the hydrogenolysis of N-benzyl moieties
  作者：David C. Johnson、Theodore S. Widlanski

  DOI：10.1016/j.tetlet.2004.09.118

  日期：2004.11

  The benzyl groups of beta-hydroxy-N-benzyl sulfonamides are labile toward hydrogenolysis-unlike N-benzyl sulfonamides lacking the beta-hydroxy moiety. We find that N-acyl-N-benzyl sulfonamides undergo hydrogenolysis under very mild conditions. Based upon these observations, we developed a reversible safety-catch method using tert-butoxycarbonyl moieties to activate N-benzyl sulfonamides toward hydrogenolysis. We also explored the utility of the safety-catch activation method for other nitrogen-based functionality such as N-benzyl carboxamides, imides, and related functionality. (C) 2004 Elsevier Ltd. All rights reserved.
• Johnson II, David C.; Widlanski, Theodore S., Synthesis, 2002, # 6, p. 809 - 815
  作者：Johnson II, David C.、Widlanski, Theodore S.

  DOI：——

  日期：——