methyl 3,4-O-isopropylidene-2-O-phenoxythiocarbonyl-β-L-arabinopyranoside | 1373340-79-4

• 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-O-phenoxythiocarbonyl-β-L-arabinopyranoside
• 英文别名: [(3aS,6S,7R,7aS)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy-phenoxymethanethione
• CAS: 1373340-79-4
• 化学式: C₁₆H₂₀O₆S
• 分子量: 340.397
• InChiKey: KXOVFNJLOBNJFL-FQUUOJAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3,4-O-isopropylidene-2-O-phenoxythiocarbonyl-β-L-arabinopyranoside 在 N-ethylpiperidine hypophosphite 、 偶氮二异丁腈 、 水 、 苯甲酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 2-脱氧-D-阿拉伯吡喃糖
  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
• 作为产物：
  描述：

  L-(+)-arabinose 在 吡啶 、 盐酸 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 methyl 3,4-O-isopropylidene-2-O-phenoxythiocarbonyl-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

• 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.