(1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol | 194220-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol
• 英文别名: (3aR,4S,6R,6aS)-2,2-dimethyl-6-(phenylmethoxyamino)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 194220-59-2
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: BKSHDYFJBDJHQY-ZOBORPQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以58%的产率得到(3aR,4S,6R,6aS)-6-氨基四氢-2,2-二甲基-4H-环戊烯并-1,3-二氧杂环戊烷-4-醇
  参考文献：
  名称：

  Synthesis and transformations of (1R,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol: synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol

  摘要：

  The synthesis and some new transformations of (1R,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol are described. Particularly relevant is the synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol 7 from D-ribonolactone, via intermediate 1, in eight steps and 12% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00236-x
• 作为产物：
  描述：

  (1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (1S,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol
  参考文献：
  名称：

  Synthesis and transformations of (1R,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol: synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol

  摘要：

  The synthesis and some new transformations of (1R,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol are described. Particularly relevant is the synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol 7 from D-ribonolactone, via intermediate 1, in eight steps and 12% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00236-x

文献信息

• Synthesis and transformations of (1R,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol: synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol
  作者：José Marco-Contelles、Ma.Mercedes Rodríguez-Fernández

  DOI：10.1016/s0957-4166(97)00236-x

  日期：1997.7

  The synthesis and some new transformations of (1R,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol are described. Particularly relevant is the synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol 7 from D-ribonolactone, via intermediate 1, in eight steps and 12% overall yield. (C) 1997 Elsevier Science Ltd.