3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-[1,4]dithiine-2-carbaldehyde | 915374-67-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-[1,4]dithiine-2-carbaldehyde
• CAS: 915374-67-3
• 化学式: C₁₁H₁₆O₃S₂
• 分子量: 260.378
• InChiKey: YIAXBQKGVDGRET-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-[1,4]dithiine-2-carbaldehyde 在 Amberlyst 15 、 镍 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.0h， 生成 [(2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
  参考文献：
  名称：

  A Versatile Route to l-Hexoses:  Synthesis of l-Mannose and l-Altrose

  摘要：

  [GRAPHICS]An efficient route for the synthesis of orthogonally protected L-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-L-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-L-pyranoside, which can be suitably functionalized to afford the desired L-hexoses. In this paper, we report the synthesis of L-manno- and L-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.

  DOI：

  10.1021/ol061916z
• 作为产物：
  描述：

  (R)-4-[3-[1-(4-Methoxy-benzyloxy)-meth-(Z)-ylidene]-[1,4]dithian-(2Z)-ylidenemethyl]-2,2-dimethyl-[1,3]dioxolane 在 silica gel 作用下， 以98%的产率得到3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-[1,4]dithiine-2-carbaldehyde
  参考文献：
  名称：

  A Versatile Route to l-Hexoses:  Synthesis of l-Mannose and l-Altrose

  摘要：

  [GRAPHICS]An efficient route for the synthesis of orthogonally protected L-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-L-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-L-pyranoside, which can be suitably functionalized to afford the desired L-hexoses. In this paper, we report the synthesis of L-manno- and L-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.

  DOI：

  10.1021/ol061916z