5-thio-α-D-ribopyranose | 15354-46-8

• 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-ribopyranose
• 英文别名: α-D-5-thio-ribopyranose；(2S,3R,4R,5S)-thiane-2,3,4,5-tetrol
• CAS: 15354-46-8
• 化学式: C₅H₁₀O₄S
• 分子量: 166.198
• InChiKey: QWVJFKXOINHVGD-AIHAYLRMSA-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-O-isopropylidene-5-thiocyanato-D-ribonofuranose 在 溶剂黄146 、 锌 作用下， 反应 3.0h， 生成 5-thio-β-D-ribopyranose 、 5-thio-α-D-ribopyranose
  参考文献：
  名称：

  An improved synthesis of 5-thio-d-ribose from d-ribono-1,4-lactone

  摘要：

  5-Thio-D-ribopyranose was synthesized from D-ribono-1,4-lactone (1) by two approaches: (i) 5-bromo-5-deoxy-D-ribono-1,4-lactone (2) was successively transformed into 5-bromo-5-deoxy, 5-S-acetyl-5-thio or 5-thiocyanato-D-ribofuranose derivatives; appropriate treattncnt then lead to 5-thin-D-ribopyranose (7) in 46-48% overall yield and; (ii) 2 was transformed into the 5-S-acetyl-5-thio-D-ribono-1,4-lactone derivative (11). Reduction and deprotection of 11 afforded 5-thio-D-ribopyranose (7) in 57% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00170-2

文献信息

• An improved synthesis of 5-thio-d-ribose from d-ribono-1,4-lactone
  作者：Jérôme Lalot、Imane Stasik、Gilles Demailly、Daniel Beaupère

  DOI：10.1016/s0008-6215(02)00170-2

  日期：2002.9

  5-Thio-D-ribopyranose was synthesized from D-ribono-1,4-lactone (1) by two approaches: (i) 5-bromo-5-deoxy-D-ribono-1,4-lactone (2) was successively transformed into 5-bromo-5-deoxy, 5-S-acetyl-5-thio or 5-thiocyanato-D-ribofuranose derivatives; appropriate treattncnt then lead to 5-thin-D-ribopyranose (7) in 46-48% overall yield and; (ii) 2 was transformed into the 5-S-acetyl-5-thio-D-ribono-1,4-lactone derivative (11). Reduction and deprotection of 11 afforded 5-thio-D-ribopyranose (7) in 57% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.