(2R,3S,4R,6R)-6-(1,5-dihydroxynaphthalen-2-yl)-2-(hydroxymethyl)oxane-3,4-diol | 727654-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3S,4R,6R)-6-(1,5-dihydroxynaphthalen-2-yl)-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 727654-83-3
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: SBEURJCVOXTLIB-KQTLUZQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,6R)-6-(1,5-dihydroxynaphthalen-2-yl)-2-(hydroxymethyl)oxane-3,4-diol 在 溴 、 三苯基膦 作用下， 反应 15.0h， 生成 (2S,3S,4R,6R)-2-Bromomethyl-6-(1,5-dihydroxy-naphthalen-2-yl)-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Synthesis of 5-aza-analogues of angucyclines: manipulation of the 2-deoxy-C-glycoside subunit

  摘要：

  Based on a heterocyclic Diels-Alder strategy, a concise synthesis of 5-aza-analogues of angucyclines bearing a 2-deoxy-C-glycoside subunit is reported. Starting from a common intermediate, a peracetylated D-2-deoxyglucose could be linked to carbons C9 or C10 of the tetracyclic framework. Further manipulations of the sugar residue allowed the installation of bromo and azido substituents at carbon C6'. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.053
• 作为产物：
  描述：

  β-D-2-deoxy-glucopyranose 、 1,5-二羟基萘 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 (2R,3S,4R,6R)-6-(1,5-dihydroxynaphthalen-2-yl)-2-(hydroxymethyl)oxane-3,4-diol
  参考文献：
  名称：

  A hetero Diels–Alder approach to the synthesis of the first angucyclinone and angucycline 5-aza-analogues

  摘要：

  The synthesis of two new heterodienes and their regioselective [4+2]cycloaddition reactions with several bromo-naphthoquinones allowed us to prepare the first angucyclinone and angucycline 5-aza-analogues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.123

文献信息

• A hetero Diels–Alder approach to the synthesis of the first angucyclinone and angucycline 5-aza-analogues
  作者：Sylvain C Collet、Jean-François Rémi、Claire Cariou、Samia Laı̈b、André Y Guingant、Nguyen Quang Vu、Gilles Dujardin

  DOI：10.1016/j.tetlet.2004.04.123

  日期：2004.6

  The synthesis of two new heterodienes and their regioselective [4+2]cycloaddition reactions with several bromo-naphthoquinones allowed us to prepare the first angucyclinone and angucycline 5-aza-analogues. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of 5-aza-analogues of angucyclines: manipulation of the 2-deoxy-C-glycoside subunit
  作者：Nguyen Quang Vu、Gilles Dujardin、Sylvain C. Collet、Eun-Ang Raiber、André Y. Guingant、Michel Evain

  DOI：10.1016/j.tetlet.2005.09.053

  日期：2005.11

  Based on a heterocyclic Diels-Alder strategy, a concise synthesis of 5-aza-analogues of angucyclines bearing a 2-deoxy-C-glycoside subunit is reported. Starting from a common intermediate, a peracetylated D-2-deoxyglucose could be linked to carbons C9 or C10 of the tetracyclic framework. Further manipulations of the sugar residue allowed the installation of bromo and azido substituents at carbon C6'. (c) 2005 Elsevier Ltd. All rights reserved.