(2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone | 1352406-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone
• 英文别名: (2S,3R,5R)-5-azido-2-[(4-methoxyphenyl)methoxy]-3-phenylmethoxycycloheptan-1-one
• CAS: 1352406-29-1
• 化学式: C₂₂H₂₅N₃O₄
• 分子量: 395.458
• InChiKey: YYEAZAQMYYYOSL-STZQEDGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone 在 氨 、 sodium 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 (1R,2S,3R,5R)-8-氮杂二环[3.2.1]辛烷-1,2,3-三醇
  参考文献：
  名称：

  Chiral pool synthesis of calystegine A3 from 2-deoxyglucose via a Brown allylation

  摘要：

  Calystegine A(3) is a naturally occurring nortropane iminosugar of which there previously have been three total syntheses. Inspired by our previous work we here report on a fourth approach using 17 steps from 2-deoxy-D-glucose applying a diastereoselective allylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.10.025
• 作为产物：
  描述：

  (1R,2R,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptan-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到(2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone
  参考文献：
  名称：

  Chiral pool synthesis of calystegine A3 from 2-deoxyglucose via a Brown allylation

  摘要：

  Calystegine A(3) is a naturally occurring nortropane iminosugar of which there previously have been three total syntheses. Inspired by our previous work we here report on a fourth approach using 17 steps from 2-deoxy-D-glucose applying a diastereoselective allylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.10.025

文献信息

• Chiral pool synthesis of calystegine A3 from 2-deoxyglucose via a Brown allylation
  作者：Tina Secher Rasmussen、Henrik Helligsø Jensen

  DOI：10.1016/j.carres.2011.10.025

  日期：2011.12

  Calystegine A(3) is a naturally occurring nortropane iminosugar of which there previously have been three total syntheses. Inspired by our previous work we here report on a fourth approach using 17 steps from 2-deoxy-D-glucose applying a diastereoselective allylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.