5,6-dideoxy-6-fluoro-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose | 1038780-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-dideoxy-6-fluoro-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose
• CAS: 1038780-48-1
• 化学式: C₉H₁₃FO₄
• 分子量: 204.198
• InChiKey: UIRAHJFDRDKWDO-ULAWRXDQSA-N

反应信息

• 作为反应物：
  描述：

  5,6-dideoxy-6-fluoro-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose 在 三氟乙酸 作用下， 以 水 为溶剂， 生成 (Z)-5,6-dideoxy-6-fluoro-D-xylo-hex-5-enofuranose 、 (E)-5,6-dideoxy-6-fluoro-D-xylo-hex-5-enofuranose
  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