3-O-benzoyl-5,6-dideoxy-6-fluoro-1,2-isopropylidene-6-tributylstannyl-α-D-xylo-hex-5-enofuranose | 1038779-87-1

• 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: 3-O-benzoyl-5,6-dideoxy-6-fluoro-1,2-isopropylidene-6-tributylstannyl-α-D-xylo-hex-5-enofuranose
• CAS: 1038779-87-1
• 化学式: C₂₈H₄₃FO₅Sn
• 分子量: 597.355
• InChiKey: IEMPGKWDEZCDLN-XRBZDIGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  35.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-O-benzoyl-5,6-dideoxy-6-fluoro-1,2-isopropylidene-6-tributylstannyl-α-D-xylo-hex-5-enofuranose 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  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

文献信息

• S-Ribosylhomocysteine analogues with the carbon-5 and sulfur atoms replaced by a vinyl or (fluoro)vinyl unit
  作者：Stanislaw F. Wnuk、Jennifer Lalama、Craig A. Garmendia、Jenay Robert、Jinge Zhu、Dehua Pei

  DOI：10.1016/j.bmc.2008.03.028

  日期：2008.5

  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.