(3aR,5R,6R,6aR)-5-((Z)-2-fluoro-2-iodovinyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol | 1038780-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6R,6aR)-5-((Z)-2-fluoro-2-iodovinyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 1038780-39-0
• 化学式: C₉H₁₂FIO₄
• 分子量: 330.095
• InChiKey: CVJUSLCNYYVSPP-ACYWEIILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-O-benzoyl-5,6-dideoxy-6-fluoro-1,2-isopropylidene-6-tributylstannyl-α-D-ribo-hex-5-enofuranose 、 bromo(4-ethoxy-4-oxobutyl)zinc 在 四(三苯基膦)钯 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 、 四氢呋喃 、 苯 为溶剂， 反应 6.0h， 以22 mg的产率得到ethyl 3-O-benzoyl-5,6,7,8,9-pentadeoxy-6-fluoro-1,2-O-isopropylidene-α-D-ribo-dec-5(Z)-enofuranuronate
  参考文献：
  名称：

  S-Ribosylhomocysteine analogues with the carbon-5 and sulfur atoms replaced by a vinyl or (fluoro)vinyl unit

  摘要：

  Treatment of the protected ribose or xylose 5-aldehyde with sulfonyl-stabilized fluorophosphonate gave (fluoro)vinyl sulfones. Stannyldesulfonylation followed by iododestannylation afforded 5,6-dideoxy-6-fluoro-6-iodo-D-ribo or xylo-hex-5-enofuranoses. Coupling of the hexenofuranoses with alkylzinc bromides gave 10-carbon ribosyl- and xylosylhomocysteine analogues incorporating a fluoroalkene. The fluoroalkenyl and alkenyl analogues were evaluated for inhibition of Bacillus subtilis S-ribosyl-homocysteinase (LuxS). One of the compounds, 3,5,6-trideoxy-6-fluoro-D-erythro-hex-5-enofuranose, acted as a competitive inhibitor of moderate potency (K(I) = 96 mu M). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.028