ethyl 3-O-benzoyl-5,6,7,8,9-pentadeoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-dec-5(Z)-enofuranuronate | 1038780-00-5

• 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: ethyl 3-O-benzoyl-5,6,7,8,9-pentadeoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-dec-5(Z)-enofuranuronate
• CAS: 1038780-00-5
• 化学式: C₂₂H₂₇FO₇
• 分子量: 422.451
• InChiKey: KUXDPVUISXIRRI-SYQSCRQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 ethyl 3-O-benzoyl-5,6,7,8,9-pentadeoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-dec-5(Z)-enofuranuronate 在 氨 作用下， 反应 48.0h， 以74%的产率得到methyl 5,6,7,8,9-pentadeoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-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
• 作为产物：
  描述：

  、 bromo(4-ethoxy-4-oxobutyl)zinc 在 四(三苯基膦)钯 作用下， 以 苯 为溶剂， 以54%的产率得到ethyl 3-O-benzoyl-5,6,7,8,9-pentadeoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-dec-5(Z)-enofuranuronate
  参考文献：
  名称：

  Novel S -Ribosylhomocysteine Analogues as Potential Inhibitors of LuxS Enzyme

  摘要：

  Selective cross-coupling of the protected 6-fluoro-6-iodo-alpha-D-ribo-hex-5-enofuranose with 2 equivalents of 4-ethoxy-4-oxobutylzinc bromide in the presence of Pd[P(Ph)(3)](4) followed by deprotections gave methyl 5,6,7,8,9-pentadeoxy-6-fluoro-alpha/beta-D-ribo-dec-5(Z)-enofuranuronate; a S-ribosylhomocysteine analogue with the sulfur and carbon-5 atoms replaced by the fluoro(vinyl) unit.

  DOI：

  10.1080/15257770701513190