((1S,2S,3R,4R,5R)-2,3,4,5-Tetrahydroxy-cyclohexyl)-acetic acid methyl ester | 140390-51-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ((1S,2S,3R,4R,5R)-2,3,4,5-Tetrahydroxy-cyclohexyl)-acetic acid methyl ester
• 英文别名: methyl 2-[(1S,2S,3R,4R,5R)-2,3,4,5-tetrahydroxycyclohexyl]acetate
• CAS: 140390-51-8
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: KOLFDDPNLVDRJR-UCRNHUTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ((3aS,4S,5aR,8aR,8bR)-2,2,7,7-Tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl)-acetic acid methyl ester 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 24.0h， 以68%的产率得到((1S,2S,3R,4R,5R)-2,3,4,5-Tetrahydroxy-cyclohexyl)-acetic acid methyl ester
  参考文献：
  名称：

  6-Exo free radical cyclization of acyclic carbohydrate intermediates: a new synthetic route to enantiomerically pure polyhydroxylated cyclohexane derivatives

  摘要：

  The 6-exo free radical cyclization of conveniently functionalized acyclic carbohydrate derivatives is a new and efficient method for the asymmetric synthesis of polyhydroxylated cyclohexane compounds (aminocyclitols, pseudosugars). The scope and versatility of this synthetic route has been analyzed by changing the absolute configuration of the radical precursors and the nature of the radical trap. The yield and stereoselectivity in this process is very structure dependent.

  DOI：

  10.1021/jo00035a017