2,3-O-cyclohexylidene (1,2,3,4,5/0)-5-acetamido-1,2,3,4-cyclopentanetetrol | 61768-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-cyclohexylidene (1,2,3,4,5/0)-5-acetamido-1,2,3,4-cyclopentanetetrol
• CAS: 61768-70-5
• 化学式: C₁₃H₂₁NO₅
• 分子量: 271.313
• InChiKey: VMSXZMKXTAONSJ-NMZKHRHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  88.02
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3-O-cyclohexylidene (1,2,3,4,5/0)-5-acetamido-1,2,3,4-cyclopentanetetrol 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 硫代氯甲酸苯酯 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 266.5h， 生成 1,2-O-cyclohexylidene (1S,2R,3R,4R)-3-acetamido-1,2,4-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
• 作为产物：
  描述：

  在 sodium acetate 作用下， 以 乙二醇甲醚 、 水 为溶剂， 反应 3.0h， 生成 2,3-O-cyclohexylidene (1,2,3,4,5/0)-5-acetamido-1,2,3,4-cyclopentanetetrol
  参考文献：
  名称：

  Synthesis of an α-mannosidase inhibitor, (±)-mannostatin A and its isomer

  摘要：

  (±)-Mannostatin A 1 是一种强效δ-±-甘露糖苷酶抑制剂，从肌醇开始，首次合成了其异构体--四-N,O-乙酰基衍生物 10 和 15。

  DOI：

  10.1039/c39910000890

文献信息

• Aminocyclitols. 34. Synthesis of Inosadiamine-1,4 Derivatives
  作者：Kinnichi Tadano、Takaaki Shiratori、Tetsuo Suami

  DOI：10.1246/bcsj.49.3193

  日期：1976.11

  Three new inosadiamine-1,4 derivatives have been prepared by nitromethane cyclization of a dialdehyde obtained by periodate oxidation of 1,4-di-O-methyl-(l,2,3,4,5/0)-5-acetamido-l,2,3,4-cyclopentanetetrol. The cyclization product was catalytically hydrogenated and subsequently acetylated to give three inosadiamine derivatives. Their structures were established by PMR spectra as myo-2,5, epi-1,4, and

  通过 1,4-二-O-甲基-(1,2,3,4,5/0)-5-乙酰胺-(1,4-二-O-甲基-(1,2,3,4,5/0)-5-乙酰氨基- l,2,3,4-环戊四醇。环化产物经催化氢化，随后乙酰化，得到三种肌二胺衍生物。它们的结构通过 PMR 光谱确定为 myo-2,5、epi-1,4 和 cis-inosadiamine-1,4 衍生物。
• 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.
• Ogawa, Seiichiro; Kimura, Hiroshi; Uchida, Chikara, Journal of the Chemical Society. Perkin transactions I, 1995, # 13, p. 1695 - 1706
  作者：Ogawa, Seiichiro、Kimura, Hiroshi、Uchida, Chikara、Ohashi, Takashi

  DOI：——

  日期：——