((3aS,7aS)-2,2-dimethyl-5-tosyl-3a,4,5,7a-tetrahydro[1,3]dioxolo[4,5-c]pyridine-6-yl)methanol | 1262323-79-4

• 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,7aS)-2,2-dimethyl-5-tosyl-3a,4,5,7a-tetrahydro[1,3]dioxolo[4,5-c]pyridine-6-yl)methanol
• 英文别名: [(3aS,7aS)-2,2-dimethyl-5-(4-methylphenyl)sulfonyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyridin-6-yl]methanol
• CAS: 1262323-79-4
• 化学式: C₁₆H₂₁NO₅S
• 分子量: 339.412
• InChiKey: BWMDFSXSZYXSKA-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((3aS,7aS)-2,2-dimethyl-5-tosyl-3a,4,5,7a-tetrahydro[1,3]dioxolo[4,5-c]pyridine-6-yl)methanol 、 乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到((3aS,7aS)-2,2-dimethyl-5-tosyl-3a,4,5,7a-tetrahydro[1,3]dioxolo[4,5-c]pyridine-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
• 作为产物：
  描述：

  N-[[(4S,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-4-methyl-N-(2-oxoethyl)benzenesulfonamide 在 L-脯氨酸 、 sodium tetrahydroborate 作用下， 以 氯仿 、 二甲基亚砜 、 甲醇 为溶剂， 反应 22.0h， 以19%的产率得到((3aS,7aS)-2,2-dimethyl-5-tosyl-3a,4,5,7a-tetrahydro[1,3]dioxolo[4,5-c]pyridine-6-yl)methanol
  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