methyl 5,6,7,8,9-pentadeoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-dec-5(Z)-enofuranuronate | 1038780-05-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5,6,7,8,9-pentadeoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-dec-5(Z)-enofuranuronate
• CAS: 1038780-05-0
• 化学式: C₁₄H₂₁FO₆
• 分子量: 304.316
• InChiKey: GXOJLYHGTAPKKL-CZRIBCMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 5,6,7,8,9-pentadeoxy-6-fluoro-1,2-O-isopropylidene-α-D-xylo-dec-5(Z)-enofuranuronate 在 三氟乙酸 作用下， 生成 5,6,7,8,9-pentadeoxy-6-fluoro-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
• 作为产物：
  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