5-deoxy-D-ribo-hexofuranose | 3253-94-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-deoxy-D-ribo-hexofuranose
• 英文别名: D-ribo-5-deoxy-hexose；ξ-D-ribo-5-deoxy-hexofuranose；5-deoxy-D-allose；(3R,4S,5R)-5-(2-hydroxyethyl)oxolane-2,3,4-triol
• CAS: 3253-94-9
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: WRYOEBBYARWGSI-JDJSBBGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-deoxy-D-ribo-hexofuranose 在 immobilised glucose isomerase 、 magnesium sulfate 作用下， 以 水 为溶剂， 反应 8.0h， 以37%的产率得到5-deoxy-D-erythro-hex-2-ulopyranose
  参考文献：
  名称：

  Synthetic applications of glucose isomerase: isomerisation of C-5-modified (2R,3R,4R)-configured hexoses into the corresponding 2-ketoses

  摘要：

  Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R,4R)-configured hexoses such as 5-deoxy-D-ribo-hexose, 5-azido-5-deoxy-D-allose, as well as the corresponding epimer at C-5, 5-azido-5-deoxy-L-talose, as substrates. From the resulting azidodeoxyketoses, 5-azido-5-deoxy-D-psico- and -L-tagatopyranose, the powerful D-galactosidase inhibitors 2,5-dideoxy-2,5-imino-D-galactital and -D-altritol were obtained in one additional step. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00119-6
• 作为产物：
  描述：

  甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 sodium hydroxide 、 pyridine-SO3 complex 、 potassium tert-butylate 、 双氧水 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 5-deoxy-D-ribo-hexofuranose
  参考文献：
  名称：

  5′-Homoaristeromycin. Synthesis and antiviral activity against orthopox viruses

  摘要：

  An efficient synthesis of 5'-homoaristeromycin has been developed. This permitted an extensive antiviral analysis, which found potent activity toward vaccinia, cowpox, and monkeypox viruses. For comparative purposes, 5'-homoadenosine was made available by a newly designed route and found to be inactive. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.019

文献信息

• Pakulski, Z.; Zamojski, A., Polish Journal of Chemistry, 1995, vol. 69, # 6, p. 912 - 917
  作者：Pakulski, Z.、Zamojski, A.

  DOI：——

  日期：——
• 5′-Homoaristeromycin. Synthesis and antiviral activity against orthopox viruses
  作者：Minmin Yang、Stewart W. Schneller

  DOI：10.1016/j.bmcl.2004.10.019

  日期：2005.1

  An efficient synthesis of 5'-homoaristeromycin has been developed. This permitted an extensive antiviral analysis, which found potent activity toward vaccinia, cowpox, and monkeypox viruses. For comparative purposes, 5'-homoadenosine was made available by a newly designed route and found to be inactive. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthetic applications of glucose isomerase: isomerisation of C-5-modified (2R,3R,4R)-configured hexoses into the corresponding 2-ketoses
  作者：Martin H. Fechter、Arnold E. Stütz

  DOI：10.1016/s0008-6215(99)00119-6

  日期：1999.6

  Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R,4R)-configured hexoses such as 5-deoxy-D-ribo-hexose, 5-azido-5-deoxy-D-allose, as well as the corresponding epimer at C-5, 5-azido-5-deoxy-L-talose, as substrates. From the resulting azidodeoxyketoses, 5-azido-5-deoxy-D-psico- and -L-tagatopyranose, the powerful D-galactosidase inhibitors 2,5-dideoxy-2,5-imino-D-galactital and -D-altritol were obtained in one additional step. (C) 1999 Elsevier Science Ltd. All rights reserved.