[(3aR,4S,5S,6aR)-5-acetamidospiro[4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-2,1'-cyclohexane]-4-yl] trifluoromethanesulfonate | 229306-03-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [(3aR,4S,5S,6aR)-5-acetamidospiro[4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-2,1'-cyclohexane]-4-yl] trifluoromethanesulfonate
• CAS: 229306-03-0
• 化学式: C₁₄H₂₀F₃NO₆S
• 分子量: 387.377
• InChiKey: NQGQNJLIZKQRDA-WHOHXGKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(3aR,4S,5S,6aR)-5-acetamidospiro[4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-2,1'-cyclohexane]-4-yl] trifluoromethanesulfonate 在 18-冠醚-6 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 48.67h， 生成 1,2-O-cyclohexylidene (1R,2R,3R,4S)-4-acetamido-3-(methylthio)-1,2-cyclopentanediol
  参考文献：
  名称：

  Synthesis and α-Mannosidase Inhibitory Activity of Three Deoxy Derivatives of Mannostatin A

  摘要：

  Three deoxy derivatives 2-4 of the alpha-mannosidase inhibitor mannostatin A (1) were synthesized, and their inhibition of Jack bean alpha-mannosidase was evaluated in order to elucidate the roles of each of the three hydroxyl groups of the inhibitor. The 1- and 2-deoxy derivatives 2 and 3 retained some inhibitory activity, although reduced by a factor of about 100 relative to the parent, whereas it was completely lost with the 3-deoxy derivative 4. Structure and activity relationships are discussed in the light of these findings.

  DOI：

  10.1002/(sici)1099-0690(200005)2000:9<1759::aid-ejoc1759>3.0.co;2-j
• 作为产物：
  描述：

  1,2-O-cyclohexylidene (1R,2R,3S,4S)-4-acetamido-3-O-[(2S)-2-O-acetylmandelyl]-1,2,3-cyclopentanetriol 在 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.83h， 生成 [(3aR,4S,5S,6aR)-5-acetamidospiro[4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-2,1'-cyclohexane]-4-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis and α-Mannosidase Inhibitory Activity of Three Deoxy Derivatives of Mannostatin A

  摘要：

  Three deoxy derivatives 2-4 of the alpha-mannosidase inhibitor mannostatin A (1) were synthesized, and their inhibition of Jack bean alpha-mannosidase was evaluated in order to elucidate the roles of each of the three hydroxyl groups of the inhibitor. The 1- and 2-deoxy derivatives 2 and 3 retained some inhibitory activity, although reduced by a factor of about 100 relative to the parent, whereas it was completely lost with the 3-deoxy derivative 4. Structure and activity relationships are discussed in the light of these findings.

  DOI：

  10.1002/(sici)1099-0690(200005)2000:9<1759::aid-ejoc1759>3.0.co;2-j

文献信息

• Synthesis and biological evaluation of α-mannosidase inhibitory activity of three deoxy derivatives of mannostatin A
  作者：Seiichiro Ogawa、Takayuki Morikawa

  DOI：10.1016/s0960-894x(99)00224-3

  日期：1999.6

  Three deoxy derivatives of alpha-mannosidase inhibitor mannostatin A have been synthesized and their inhibitory activity for Jack beans alpha-mannosidase evaluated in order to elucidate roles of each hydroxyl groups of the inhibitor. The 1- and 2-deoxy derivatives have preserved inhibitory potentials although they lowered the activity one-hundred fold compared to the parent, but the 3-deoxy derivative lost activity. (C) 1999 Elsevier Science Ltd. All rights reserved.