(1S,2S,4R,5S)-6-fluorocyclohexane-1,2,3,4,5-pentol | 120444-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,4R,5S)-6-fluorocyclohexane-1,2,3,4,5-pentol
• 英文别名: D-3-deoxy-3-fluoro-myo-inositol；(-)-1L-1-deoxy-1-fluoro-myo-inositol；1-L-1-deoxy-1-fluoro-myo-inositol；1D-3-deoxy-3-fluoro-myo-inositol；3-deoxy-3-fluoro-D-myo-inositol；D-3-Desoxy-3-fluor-myo-inosit
• CAS: 120444-24-8
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: PDTJJYSBSOKEOY-XCMZKKERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.86
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101.15
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,5S)-6-fluorocyclohexane-1,2,3,4,5-pentol 在 platinum(IV) oxide 吡啶 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 氢气 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 118.67h， 生成 Phosphoric acid mono-((1S,2S,3S,4S,5R,6S)-3-fluoro-2,6-dihydroxy-4,5-bis-phosphonooxy-cyclohexyl) ester
  参考文献：
  名称：

  Synthesis of the first optically pure, fluorinated inositol 1,4,5-trisphosphate of myo-inositol. Stereochemistry and its effect on calcium(2+) release in Swiss 3T3 cells

  摘要：

  DOI：

  10.1021/ja00176a055
• 作为产物：
  描述：

  D-3-Deoxy-3-fluoro-4-O-methyl-myo-inositol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (1S,2S,4R,5S)-6-fluorocyclohexane-1,2,3,4,5-pentol
  参考文献：
  名称：

  A simplified route to the phosphatidylinositol cascade inhibitor --- (-)-1L-1-deoxy-1-fluoro-Myo-inositol

  摘要：

  DOI：

  10.1016/s0040-4039(00)99246-3

文献信息

• A synthesis of (–)-1<scp>L</scp>-1-deoxy-1-fluoro-myo-inositol; a compound of potential use in sorting out the phosphatidylinositol response
  作者：Alan P. Kozikowski、Yan Xia、James M. Rusnak

  DOI：10.1039/c39880001301

  日期：——

  A synthesis of 1L-1-deoxy-1-fluoro-myo-inositol in optically pure form starting from myo-inositol is reported.

  的1的合成大号-1-脱氧-1-氟肌肉光学纯形式从开始肌醇肌醇报道肌醇。
• Synthesis of some deoxy-fluoro analogues of myo-inositol
  作者：John L. Offer、James C. Metcalfe、Gerry A. Smith

  DOI：10.1039/c39900001312

  日期：——

  Syntheses of 5-deoxy-5-fluoro-myo-inositol and optically pure 1-L- and 1-D-1-deoxy-1-fluoro-1-fluoro-myo-inositol from myo-inositol are reported as being formed in high yield.

  的合成5-脱氧-5-氟肌醇肌醇和光学纯的1-大号-和1- d -1脱氧-1-氟-1-氟-肌从肌醇肌醇肌醇被报告为形成于高产。
• Synthesis of novel metabolically stable analogues of D-myo-inositol 1,4,5-trisphosphate
  作者：Abdul H. Fauq、Javid H. Zaidi、Robert A. Wilcox、Girlie Varvel、Stefan R. Nahorski、Alan P. Kozikowski、Christophé Erneux

  DOI：10.1016/0040-4039(96)00169-4

  日期：1996.3

  Starting from L-quebrachitol, syntheses and biological activities of three novel analogues of the cellular second messenger D-myo-inositol 1,4,5-trisphosphate (IP3), 1,4-bisphosphate 5-phosphorothioate (1a), 1,5-bisphosphate 4-phosphorothioate (1b), and 1-phosphate 4,5-bisphosphorothioate (1c) are described.

  从L-quebrachitol开始，细胞第二种信使D-肌醇1,3,4,5-三磷酸（IP 3），1,4-二磷酸5-硫代磷酸酯（1a），1的三种新型类似物的合成和生物学活性描述了5-二磷酸4-磷酸硫代磷酸酯（1b）和1-磷酸4,5-二磷酸硫代磷酸酯（1c）。
• Offer, John L.; Voorheis, H. Paul; Metcalfe, James C., Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 953 - 960
  作者：Offer, John L.、Voorheis, H. Paul、Metcalfe, James C.、Smith, Gerry A.

  DOI：——

  日期：——
• Synthesis and Biological Activity of the D-3-Deoxy-3-fluoro and D-3-Chloro-3-deoxy Analogs of Phosphatidylinositol
  作者：Alan P. Kozikowski、Garth Powis、Abdul H. Fauq、Werner Tuckmantel、Alfred Gallegos

  DOI：10.1021/jo00084a010

  日期：1994.3

  The naturally occurring inositol derivative, L-quebrachitol (1), serves as starting material for the synthesis of D-3-deoxy-3-fluoro- and D-3-chloro-3-deoxy-myo-inositol (4, 28). Their transformation into the title compounds 22 and 40 (abbreviated as FPI and CPI, respectively) is accomplished by benzylation of all hydroxyl groups but OH-1 to which the phosphatidic acid side chain is subsequently attached using the phosphoramidite protocol, and hydrogenolytic deprotection. Compounds 4 and 28, as reported earlier, exhibit moderate and high selectivity, respectively, in the growth inhibition of v-sis transformed vs wild type murine NIH 3T3 cells if myo-inositol is absent but are inactive in the presence of physiological inositol levels. On the other hand, FPI possesses a nearly 2 orders of magnitude higher activity but no selectivity both in the absence or presence of myo-inositol. CPI is inactive as is the simplified analogue 24 of FPI in which the phosphatidic acid moiety has been replaced by an octadecyl group.