D-3-Deoxy-3-fluoro-4-O-methyl-myo-inositol | 125290-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-3-Deoxy-3-fluoro-4-O-methyl-myo-inositol
• 英文别名: L-1-deoxy-1-fluoro-6-O-methyl-myo-inositol；(1R,2S,3S,4S,5S,6S)-5-fluoro-6-methoxycyclohexane-1,2,3,4-tetrol
• CAS: 125290-99-5
• 化学式: C₇H₁₃FO₅
• 分子量: 196.176
• InChiKey: LZTOLKGFEOZIFP-NLZQRBTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-3-Deoxy-3-fluoro-4-O-methyl-myo-inositol 在 盐酸 、 camphor-10-sulfonic acid 三溴化硼 、 sodium hydride 、 二正丁基氧化锡 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成
  参考文献：
  名称：

  Synthesis and Biological Activity of the D-3-Deoxy-3-fluoro and D-3-Chloro-3-deoxy Analogs of Phosphatidylinositol

  摘要：

  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 CPI is inactive as is the simplified analogue 24 of FPI in which the phosphatidic acid moiety has been replaced by an octadecyl group.

  DOI：

  10.1021/jo00084a010
• 作为产物：
  描述：

  L-白雀木醇 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到D-3-Deoxy-3-fluoro-4-O-methyl-myo-inositol
  参考文献：
  名称：

  环醇化学中非经典单双差向异构化之间的竞争

  摘要：

  在四个 cyclitol 中研究了两个竞争性区域选择性和立体选择性差向异构化反应，其特征在于四个连续的 OH 基团具有顺-反-反序列，以及与该四醇单元相邻的不同取代基（OMe、OBz、F、H）。起始材料由 L-白木糖醇（化合物 5-7）和肌醇（化合物 8）合成。它们与氯醛/DCC 试剂系统的缩醛化得到具有一个差向异构化手性环原子和两个差向异构化手性中心的环状缩醛。单差向异构化仅发生在四醇序列（产物 15、17、19/20 和 24-27）中顺反三醇单元的中间 C 原子上，而双差向异构化发生在两个“中心位置” " 顺-反-反四醇单元中的碳原子（产物 16、18、21 和 28）。单、双反转化合物的产物比例变化如下：与四醇单元相邻的取代基的吸电子效应越低，相应双反转产物的百分比越高。但是，在所有情况下，单倒置产品仍然是主要产品。对原料 1-氟-2-O-(甲基)环己烷-2,3,4,5,6-戊醇 (5)

  DOI：

  10.1002/ejoc.200300688

文献信息

• Concentrated hydriodic acid in simultaneous deprotections of multifunctional inositols
  作者：Ralf Miethchen、Andreas Schmidt、Katharina Neitzel、Manfred Michalik、Thomas Pundt、Wolfgang Ruth

  DOI：10.1016/j.carres.2004.11.031

  日期：2005.3

  L-1-Deoxy-1-fluoro-6-O-methyl-myo-inositol was epimerized by chloral/DCC in boiling 1,2-dichloroethane yielding D-1-O-cyclohexylcarbaramoyl-2-deoxy-2-fluoro-3-O-methyl-5,6-O-[(R/S)-2,2,2-trichloroethylidene]-chiro-inositol. The latter and L-4-O-benzyl-3-O-cyclohexylcarbamoyl-5-O-methyl-1,2-O-(2,2,2-trichloroethylidene)-muco-inositol, L-4-O-benzyl-3-O-cyclohexylcarbamoyl-1,2-O-ethylidene-5-O-methyl-chiro-inositol, D-1-O-cyclohexylcarbamoyl-2-deoxy-5,6-O-ethylidene-2-fluoro-3-O-methyl-chiro-inositol, as well as D-5-O-benzyl-4-O-cyclohexylcarbamoyl-3-deoxy-3-(N,N'-dicyclohexylureido)-6-O-methyl-1,2-O-(2,2,2-trichloroethylidene)-chiro-inositol were deprotected with boiling 57% aq hydrogen iodide. Ether, urethane and ethylidene acetal functions were simultaneously cleaved by the reagent, whereas the trichloroethylidene groups were still intact or were only removed ill small quantities. Especially, the urea function of D-5-O-benzyl-4-O-cyclohexylcarbamoyl-3-deoxy-3-(N,N'-dicyclohexylureido)-6-O-methyl-1,2-O-(2,2,2-trichloroethylidene)-chiro-inositol was decomposed to a cyclohexylamino, group. The hydrodechlorination of D-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro-3-O-methyl-5,6-O-[(R/S)-2,2,2-trichloroethylidene]-chiro-inositol using Raney-Nickel yielded a mixture of the corresponding 5,6-O-ethylidene- and 5,6-O-chloroethylidene derivatives. The three synthetic steps-hydrodehalogenation, HI-deprotection and peracylation- were combined without purification of the intermediates. (c) 2005 Elsevier Ltd. All rights reserved.
• A simplified route to the phosphatidylinositol cascade inhibitor --- (-)-1L-1-deoxy-1-fluoro-Myo-inositol
  作者：Alan P. Kozikowski、Abdul H. Fauq、James M. Rusnak

  DOI：10.1016/s0040-4039(00)99246-3

  日期：1989.1
• d-2-Deoxy-2-fluoro-chiro-inositol—a new member of the deoxy fluoro inositol family
  作者：Ralf Miethchen、Thomas Pundt、Manfred Michalik

  DOI：10.1016/j.tetlet.2004.11.158

  日期：2005.1

  An efficient synthetic route to D-2-deoxy-2-fluoro-chiro-inositol has been developed with inversions of the C-1 and C-5 configuration of L-quebrachitol. The key steps of the route are two consecutive one pot epimerization procedure which do not require time-consuming protecting groups chemistry. (C) 2004 Elsevier Ltd. All rights reserved.