(3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-methanol | 105265-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-methanol
• 英文别名: [(3aR,6aS)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]methanol
• CAS: 105265-93-8
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: IXSDLROPEDDHSF-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-methanol 在 sodium azide 、 B2H6-THF 、 sodium hydride 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 34.0h， 生成 (1S,2S,3S,5S)-1-benzyl-5-azidomethyl-1,2,3-cyclopentanetriol
  参考文献：
  名称：

  Highly Substituted Cyclopentane–CMP Conjugates as Potent Sialyltransferase Inhibitors

  摘要：

  Sialylconjugates on cell surfaces are involved in many biological events such as cellular recognition, signal transduction, and immune response. It has been reported that aberrant sialylation at the nonreducing end of glycoconjugates and overexpression of sialyltransferases (STs) in cells are correlated with the malignance, invasion, and metastasis of tumors. Therefore, inhibitors of STs would provide valuable leads for the discovery of antitumor drugs. On the basis of the transition state of the enzyme-catalyzed sialylation reaction, we proposed that the cydopentane skeleton in its two puckered conformations might mimic the planar structure of the donor (CMP-Neu5Ac) in the transition state. A series of cydopentane-containing compounds were designed and synthesized by coupling different cydopentane alpha-hydroxyphosphonates with cytidine phosphoramidite. Their inhibitory activities against recombinant human ST6Gal-I were assayed, and a potent inhibitor 481 with a K-i of 0.028 +/- 0.006 mu M was identified. The results show that the cydopentanoid-type compounds could become a new type of sialyltransferase inhibitors as biological probes or drug leads.

  DOI：

  10.1021/acs.jmedchem.5b01181
• 作为产物：
  描述：

  4-O-[(tert-butyl)diphenylsilyl]-2,3-O-isopropylidene-D-erythrose 在 sodium tetrahydroborate 、 四丁基氟化铵 、 乙酸酐 、 二异丁基氢化铝 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 反应 48.0h， 生成 (3R,4S)-3,4-(isopropylidenedioxy)-1-cyclopentene-1-methanol
  参考文献：
  名称：

  A NEW TRANSFORMATION OF ALDOSE DERIVED SYNTHONS TO PSEUDO-HEXOPYRANOSE OR PSEUDO-PENTOFURANOSE DERIVATIVES

  摘要：

  源自于d-核糖或d-赤藓糖的无环合成物，在C-1位拥有一个2-马隆基碳链，经过立体选择性环化形成了六元或五元碳环。这些碳环有效地转化为伪-β-l-甘露糖吡喃糖衍生物或伪-β-l-阿拉伯糖呋喃糖衍生物。

  DOI：

  10.1246/cl.1986.1081

文献信息

• A novel transformation of four aldoses to some optically pure pseudohexopyranoses and a pseudopentofuranose, carbocyclic analogs of hexopyranoses and pentofuranose. Synthesis of derivatives of (1S,2S,3R,4S,5S)-, (1S,2S,3R,4R,5S)-, (1R,2R,3R,4R,5S)-, (1S,2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-1-(hydroxymethyl)cyclohexanes and (1S,2S,3S,4S)-2,3,4-trihydroxy-1(hydroxymethyl)cyclopentane
  作者：Kinichi Tadano、Hiroo Maeda、Masahide Hoshino、Youichi Iimura、Tetsuo Suami

  DOI：10.1021/jo00386a011

  日期：1987.5