methyl 3,4-O-isopropylidene-2-deoxy-β-L-arabinopyranoside | 64429-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 3,4-O-isopropylidene-2-deoxy-β-L-arabinopyranoside
• 英文别名: (3aS,6S,7aR)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 64429-68-1
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: IUUAVSYYQZOSFD-CSMHCCOUSA-N

物化性质

• 沸点：
  239.4±40.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3,4-O-isopropylidene-2-deoxy-β-L-arabinopyranoside 在 盐酸 、 水 、 溶剂黄146 作用下， 反应 89.0h， 生成 甲基-2-脱氧-L-赤式戊呋喃糖
  参考文献：
  名称：

  Improved Synthesis of 2-Deoxy-L-ribose

  摘要：

  Improved synthesis of 2-deoxy-L-ribose and the corresponding 2-deoxy-3,5-di-O-p-toluoyl-alpha-L-elythro-pentofuranosyl chloride are described from L-arabinose.

  DOI：

  10.1080/07328319908044612
• 作为产物：
  描述：

  L-(+)-arabinose 在 吡啶 、 盐酸 、 N-ethylpiperidine hypophosphite 、 偶氮二异丁腈 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.5h， 生成 methyl 3,4-O-isopropylidene-2-deoxy-β-L-arabinopyranoside
  参考文献：
  名称：

  Improved and Practical Synthesis of 2-Deoxy-L-ribose by Hypophosphite-Mediated Deoxygenation

  摘要：

  An improved and practical route for a large-scale synthesis of 2-deoxy-L-ribose starting from L-arabinose has been developed. This is the first reported synthesis of 2-deoxy-L-ribose in which deoxygenation has been mediated by hypophosphite reagents instead of by organotin reagents.

  DOI：

  10.1080/00397911.2010.520402

文献信息

• GOLIK, J.;WONG, H.;VYAS, D. M.;DOYLE, T. W., TETRAHEDRON LETT., 30,(1989) N9, C. 2497-2500
  作者：GOLIK, J.、WONG, H.、VYAS, D. M.、DOYLE, T. W.

  DOI：——

  日期：——
• Improved Synthesis of 2-Deoxy-L-ribose
  作者：Weijian Zhang、Kanda S. Ramasamy、Devron R. Averett

  DOI：10.1080/07328319908044612

  日期：1999.11

  Improved synthesis of 2-deoxy-L-ribose and the corresponding 2-deoxy-3,5-di-O-p-toluoyl-alpha-L-elythro-pentofuranosyl chloride are described from L-arabinose.
• Improved and Practical Synthesis of 2-Deoxy-L-ribose by Hypophosphite-Mediated Deoxygenation
  作者：Li-Li Chen、Xun Ming、Jun-Da Cen

  DOI：10.1080/00397911.2010.520402

  日期：2012.1.1

  An improved and practical route for a large-scale synthesis of 2-deoxy-L-ribose starting from L-arabinose has been developed. This is the first reported synthesis of 2-deoxy-L-ribose in which deoxygenation has been mediated by hypophosphite reagents instead of by organotin reagents.