5-thio-α-D-xylopyranose | 70267-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 5-thio-α-D-xylopyranose
• 英文别名: α-D-5-thio-xylopyranose；(2S,3R,4S,5S)-thiane-2,3,4,5-tetrol
• CAS: 70267-99-1
• 化学式: C₅H₁₀O₄S
• 分子量: 166.198
• InChiKey: QWVJFKXOINHVGD-LECHCGJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-di-O-acetyl-5-S-acetyl-5-thio-D-xylofuranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 5-thio-α-D-xylopyranose 、 5-thio-β-D-xylopyranose
  参考文献：
  名称：

  Efficient synthesis of 5-thio-d-arabinopyranose and 5-thio-d-xylopyranose from the corresponding d-pentono-1,4-lactones

  摘要：

  5-Thio-D-arabinopyranose (5) and 5-thio-D-xylopyranose (10) were synthesized from the corresponding D-pentono-1,4-lactones. After regioselective bromination at C-5, transformation into 5-S-acetyl-5-thio derivatives, reduction into lactols and deprotection afforded the title compounds in 49 and 42% overall yield, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00372-0

文献信息

• Efficient synthesis of 5-thio-d-arabinopyranose and 5-thio-d-xylopyranose from the corresponding d-pentono-1,4-lactones
  作者：Jérôme Lalot、Imane Stasik、Gilles Demailly、Daniel Beaupère

  DOI：10.1016/s0008-6215(03)00372-0

  日期：2003.10

  5-Thio-D-arabinopyranose (5) and 5-thio-D-xylopyranose (10) were synthesized from the corresponding D-pentono-1,4-lactones. After regioselective bromination at C-5, transformation into 5-S-acetyl-5-thio derivatives, reduction into lactols and deprotection afforded the title compounds in 49 and 42% overall yield, respectively. (C) 2003 Elsevier Ltd. All rights reserved.