methyl 3,6-anhydro-2,4-di-O-phenoxythiocarbonyl-β-D-galactopyranoside | 137013-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,6-anhydro-2,4-di-O-phenoxythiocarbonyl-β-D-galactopyranoside
• 英文别名: [(1R,3R,4R,5S,8S)-3-methoxy-4-phenoxycarbothioyloxy-2,6-dioxabicyclo[3.2.1]octan-8-yl]oxy-phenoxymethanethione
• CAS: 137013-10-6
• 化学式: C₂₁H₂₀O₇S₂
• 分子量: 448.518
• InChiKey: SJKSORATVMANNW-ICBNADEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 3,6-anhydro-2,4-di-O-phenoxythiocarbonyl-β-D-galactopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以46%的产率得到methyl 3,6-anhydro-2,4-dideoxy-β-D-threo-hexopyranoside
  参考文献：
  名称：

  Bis-deoxygenation of methyl 3,6-anhydro-D-pyranosides

  摘要：

  The synthesis and radical reduction of thiocarbonyl derivatives of methyl 3,6-anhydro pyranosides has been studied in the alpha-D-gluco, alpha-D-manno and beta-D-galacto series. A cyclic intermediate is proposed to explain the fact that bis-deoxygenation only occurred in the galactose series, providing a 3 step synthesis of the desired product 1b.

  DOI：

  10.1016/s0040-4020(01)86566-2
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 吡啶 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 methyl 3,6-anhydro-2,4-di-O-phenoxythiocarbonyl-β-D-galactopyranoside
  参考文献：
  名称：

  Bis-deoxygenation of methyl 3,6-anhydro-D-pyranosides

  摘要：

  The synthesis and radical reduction of thiocarbonyl derivatives of methyl 3,6-anhydro pyranosides has been studied in the alpha-D-gluco, alpha-D-manno and beta-D-galacto series. A cyclic intermediate is proposed to explain the fact that bis-deoxygenation only occurred in the galactose series, providing a 3 step synthesis of the desired product 1b.

  DOI：

  10.1016/s0040-4020(01)86566-2