1,2-O-cyclohexylidene (1R,2R,3R,4S,5S)-5-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-3-O-phenoxythiocarbonyl-1,2,3,4-cyclopentanetetrol | 229306-16-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2-O-cyclohexylidene (1R,2R,3R,4S,5S)-5-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-3-O-phenoxythiocarbonyl-1,2,3,4-cyclopentanetetrol
• 英文别名: [(3aR,4S,5S,6S,6aR)-6-acetamido-4-phenoxycarbothioyloxyspiro[4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-2,1'-cyclohexane]-5-yl] (2S)-2-acetyloxy-2-phenylacetate
• CAS: 229306-16-5
• 化学式: C₃₀H₃₃NO₉S
• 分子量: 583.659
• InChiKey: NKEIHSDFZVSGBV-VQVLGOAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2-O-cyclohexylidene (1R,2R,3R,4S,5S)-5-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-3-O-phenoxythiocarbonyl-1,2,3,4-cyclopentanetetrol 在 吡啶 、 盐酸 、 18-冠醚-6 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 55.5h， 生成 (1S,2R,3S,4S)-3-amino-4-methylthio-1,2-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
• 作为产物：
  描述：

  (S)-(+)-α-乙酰氧基苯乙酸 在 4-二甲氨基吡啶 、 硫代氯甲酸苯酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 265.5h， 生成 1,2-O-cyclohexylidene (1R,2R,3R,4S,5S)-5-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-3-O-phenoxythiocarbonyl-1,2,3,4-cyclopentanetetrol
  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