benzyl N-[(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-5-hydroxypentyl]-N-benzylcarbamate | 1255906-14-9

• 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: benzyl N-[(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-5-hydroxypentyl]-N-benzylcarbamate
• CAS: 1255906-14-9
• 化学式: C₂₇H₃₅NO₆
• 分子量: 469.578
• InChiKey: NVEYQWMAIWZVJA-CXSMSNRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-[(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-5-hydroxypentyl]-N-benzylcarbamate 在 palladium 10% on activated carbon 、 氢气 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  The synthesis of (1S,8aS)-1-hydroxyindolizidine using a stereoselective Grignard addition to an N-benzyl-3-deoxy sugar imine derived from D-Glucose

  摘要：

  A highly stereoselective approach to 1-hydroxyindolizidine is described using a Grignard reaction on N-benzyl imine derived from 3-deoxy-1,2-O-isopropylidine-alpha-D-xylo-pentodialdofuranose and reductive cyclization as key steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.08.001
• 作为产物：
  描述：

  在 dimethyl sulfide borane 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以93%的产率得到benzyl N-[(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-5-hydroxypentyl]-N-benzylcarbamate
  参考文献：
  名称：

  The synthesis of (1S,8aS)-1-hydroxyindolizidine using a stereoselective Grignard addition to an N-benzyl-3-deoxy sugar imine derived from D-Glucose

  摘要：

  A highly stereoselective approach to 1-hydroxyindolizidine is described using a Grignard reaction on N-benzyl imine derived from 3-deoxy-1,2-O-isopropylidine-alpha-D-xylo-pentodialdofuranose and reductive cyclization as key steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.08.001

文献信息

• The synthesis of (1S,8aS)-1-hydroxyindolizidine using a stereoselective Grignard addition to an N-benzyl-3-deoxy sugar imine derived from D-Glucose
  作者：Y. Jagadeesh、B. Chandrasekhar、B. Venkateswara Rao

  DOI：10.1016/j.tetasy.2010.08.001

  日期：2010.9

  A highly stereoselective approach to 1-hydroxyindolizidine is described using a Grignard reaction on N-benzyl imine derived from 3-deoxy-1,2-O-isopropylidine-alpha-D-xylo-pentodialdofuranose and reductive cyclization as key steps. (C) 2010 Elsevier Ltd. All rights reserved.