((3aS,6S,7R,7aS)-7-acetoxy-2,2-dimethyl-5-tosylhexahydro[1,3]dioxolo[4,5-c]pyridin-6-yl)methyl acetate | 1262323-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((3aS,6S,7R,7aS)-7-acetoxy-2,2-dimethyl-5-tosylhexahydro[1,3]dioxolo[4,5-c]pyridin-6-yl)methyl acetate
• 英文别名: [(3aS,6S,7R,7aR)-7-acetyloxy-2,2-dimethyl-5-(4-methylphenyl)sulfonyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridin-6-yl]methyl acetate
• CAS: 1262323-80-7
• 化学式: C₂₀H₂₇NO₈S
• 分子量: 441.502
• InChiKey: HRUIIYSHSPORGX-INDMIFKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (3aS,6S,7R,7aS)-6-(hydroxymethyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxolo[4,5-c]pyridin-7-ol 、 乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到((3aS,6S,7R,7aS)-7-acetoxy-2,2-dimethyl-5-tosylhexahydro[1,3]dioxolo[4,5-c]pyridin-6-yl)methyl acetate
  参考文献：
  名称：

  Proline catalyzed direct diastereoselective 6-enolexo aldolization: toward the synthesis of the imino sugar DNJ

  摘要：

  A L-proline catalyzed direct diastereoselective 6-enolexo aldolization reaction of differentiating dialdehydes derived from tartaric acid is presented This organocatalytic approach provides high levels of synselectivity (dr > 10 1) with the stereocontrolled C-C bond formation between C4 and C5 intramolecularly which can serve to synthesize Imino-sugar skeleton quickly (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.024