(2R,6R)-di-tert-butyl-2,6-bis((tert-butyldimethylsilyloxy)methyl)-4-chloro-2,3,5,6-tetrahydrodipyrrolo[2,3-b:3',2'-e]pyridine-1,7-dicarboxylate | 1361336-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (2R,6R)-di-tert-butyl-2,6-bis((tert-butyldimethylsilyloxy)methyl)-4-chloro-2,3,5,6-tetrahydrodipyrrolo[2,3-b:3',2'-e]pyridine-1,7-dicarboxylate
• 英文别名: ditert-butyl (5R,11R)-5,11-bis[[tert-butyl(dimethyl)silyl]oxymethyl]-8-chloro-2,4,12-triazatricyclo[7.3.0.03,7]dodeca-1,3(7),8-triene-4,12-dicarboxylate
• CAS: 1361336-01-7
• 化学式: C₃₃H₅₈ClN₃O₆Si₂
• 分子量: 684.464
• InChiKey: LVOXCYXJQCFOPJ-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.11
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,6R)-di-tert-butyl-2,6-bis((tert-butyldimethylsilyloxy)methyl)-4-chloro-2,3,5,6-tetrahydrodipyrrolo[2,3-b:3',2'-e]pyridine-1,7-dicarboxylate 在 三氟乙酸 作用下， 反应 3.0h， 以83.9%的产率得到((2R,6R)-4-chloro-1,2,3,5,6,7-hexahydrodipyrrolo[2,3-b:3',2'-e]pyridine-2,6-diyl)dimethanol
  参考文献：
  名称：

  Iterative One Pot Reactions of a Chiral Sulfamidate with 2,4,6-Trichloropyridine: Regiocontrolled Synthesis of Linear and Angular Chiral Dipyrrolidino Pyridines

  摘要：

  The product of the ring opening of a chiral sulfamidate with the 3-lithiopyridine species obtained by deprotonation of 2,4,6-trichloropyridine with n-BuLi can be deprotonated again in situ with n-BuLi and reacted with a second equivalent of the sulfamidate furnishing a bis beta-aminoethyl pyridine derivative which can be cyclized regioselectively to linear or angular chiral dipyrrolidino pyridines.

  DOI：

  10.3987/com-11-12360
• 作为产物：
  描述：

  2,4,6-三氯吡啶 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (2R,6R)-di-tert-butyl-2,6-bis((tert-butyldimethylsilyloxy)methyl)-4-chloro-2,3,5,6-tetrahydrodipyrrolo[2,3-b:3',2'-e]pyridine-1,7-dicarboxylate 、 (2R,7R)-di-tert-butyl 2,7-bis[(tert-butyldimethylsilyloxy)methyl]-4-chloro-2,3,7,8-tetrahydrodipyrrolo[2,3-b:2',3'-d]pyridine-1,6-dicarboxylate
  参考文献：
  名称：

  Iterative One Pot Reactions of a Chiral Sulfamidate with 2,4,6-Trichloropyridine: Regiocontrolled Synthesis of Linear and Angular Chiral Dipyrrolidino Pyridines

  摘要：

  The product of the ring opening of a chiral sulfamidate with the 3-lithiopyridine species obtained by deprotonation of 2,4,6-trichloropyridine with n-BuLi can be deprotonated again in situ with n-BuLi and reacted with a second equivalent of the sulfamidate furnishing a bis beta-aminoethyl pyridine derivative which can be cyclized regioselectively to linear or angular chiral dipyrrolidino pyridines.

  DOI：

  10.3987/com-11-12360

文献信息

• Iterative One Pot Reactions of a Chiral Sulfamidate with 2,4,6-Trichloropyridine: Regiocontrolled Synthesis of Linear and Angular Chiral Dipyrrolidino Pyridines
  作者：Paul Hebeisen、André Alker、Markus Buerkler

  DOI：10.3987/com-11-12360

  日期：——

  The product of the ring opening of a chiral sulfamidate with the 3-lithiopyridine species obtained by deprotonation of 2,4,6-trichloropyridine with n-BuLi can be deprotonated again in situ with n-BuLi and reacted with a second equivalent of the sulfamidate furnishing a bis beta-aminoethyl pyridine derivative which can be cyclized regioselectively to linear or angular chiral dipyrrolidino pyridines.