(2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)pyrrolidine hydrochloride | 1431371-94-6

• 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: (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)pyrrolidine hydrochloride
• CAS: 1431371-94-6
• 化学式: C₂₆H₂₉NO₃*ClH
• 分子量: 439.982
• InChiKey: QOJDXOSBEIHCHH-FYBPOUACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  39.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)pyrrolidine hydrochloride 在 palladium on activated charcoal 、 氢气 作用下， 以97%的产率得到1,4-二脱氧-1,4-亚氨基-D-核糖醇
  参考文献：
  名称：

  Effective and one-step stereo-controlled synthesis of benzyloxylated-diiodopentanes for the synthesis of five-membered imino-sugars

  摘要：

  An effective and stereo-controlled synthesis of 1,3,4-tris(benzyloxy)-2,5-diiodopentane starting from 2,3,5-tris(benzyloxy)pentane-1,4-diol was reported. Synthesis was improved to get the diiodide compound instead of forming the ring-closure product (benzyloxylated tetrahydrofuran). From the diiodide intermediate, the five-membered aza-sugar was synthesized with high yield. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.115
• 作为产物：
  描述：

  2,3,5-tri-O-benzyl-D-ribitol 在 甲醇 、 sodium azide 、 水 、 碘 、 乙酰氯 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 53.0h， 生成 (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)pyrrolidine hydrochloride
  参考文献：
  名称：

  Effective and one-step stereo-controlled synthesis of benzyloxylated-diiodopentanes for the synthesis of five-membered imino-sugars

  摘要：

  An effective and stereo-controlled synthesis of 1,3,4-tris(benzyloxy)-2,5-diiodopentane starting from 2,3,5-tris(benzyloxy)pentane-1,4-diol was reported. Synthesis was improved to get the diiodide compound instead of forming the ring-closure product (benzyloxylated tetrahydrofuran). From the diiodide intermediate, the five-membered aza-sugar was synthesized with high yield. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.115