ethyl 3-O-benzoyl-6-[3-(ethoxycarbonyl)propyl]-5,6,7,8,9-pentadeoxy-1,2-O-isopropylidene-α-D-xylo-dec-5-enofuranuronate | 1038779-77-9

• 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-6-[3-(ethoxycarbonyl)propyl]-5,6,7,8,9-pentadeoxy-1,2-O-isopropylidene-α-D-xylo-dec-5-enofuranuronate
• CAS: 1038779-77-9
• 化学式: C₂₈H₃₈O₉
• 分子量: 518.604
• InChiKey: UCLCTXXTPIOPHM-YNZATZHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  37.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  3-O-benzoyl-5,6-dideoxy-6,6-dibromo-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose 、 bromo(4-ethoxy-4-oxobutyl)zinc 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 6.0h， 以48%的产率得到ethyl 3-O-benzoyl-6-[3-(ethoxycarbonyl)propyl]-5,6,7,8,9-pentadeoxy-1,2-O-isopropylidene-α-D-xylo-dec-5-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