(1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol | 229306-13-2

• 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: (1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol
• 英文别名: [(1R,2R,3S,4S)-3-acetamido-2-methylsulfanyl-4-(phenylcarbamoyloxy)cyclopentyl] acetate
• CAS: 229306-13-2
• 化学式: C₁₇H₂₂N₂O₅S
• 分子量: 366.438
• InChiKey: CEMKGRJERPCNQL-FZKCQIBNSA-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：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 Acetic acid (1R,2R,3S,4S)-3-acetylamino-4-hydroxy-2-methylsulfanyl-cyclopentyl ester
  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：

  Phenyl-carbamic acid (1R,2S,3R,4R,5S)-2-acetylamino-4,5-dihydroxy-3-methylsulfanyl-cyclopentyl ester 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲苯 、 乙腈 、 苯 为溶剂， 反应 3.0h， 生成 (1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol
  参考文献：
  名称：

  Synthesis and biological evaluation of α-mannosidase inhibitory activity of three deoxy derivatives of mannostatin A

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(99)00224-3