(1S,2R,3R,4S,5R,6S)-2-fluoro-3,4,5,6-tetrakis(phenylmethoxy)cyclohexan-1-ol | 120444-22-6

• 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: (1S,2R,3R,4S,5R,6S)-2-fluoro-3,4,5,6-tetrakis(phenylmethoxy)cyclohexan-1-ol
• CAS: 120444-22-6
• 化学式: C₃₄H₃₅FO₅
• 分子量: 542.647
• InChiKey: WGEHYWFSBAORNM-PBNHZRHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,4S,5R,6S)-2-fluoro-3,4,5,6-tetrakis(phenylmethoxy)cyclohexan-1-ol 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (1R,2R,3S,4R,5S,6S)-2,3,4,5-Tetrakis-benzyloxy-6-fluoro-cyclohexanol
  参考文献：
  名称：

  （–）-1L-1-脱氧-1-氟-肌醇的合成；一种潜在的化合物，可用于清除磷脂酰肌醇反应

  摘要：

  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。

  DOI：

  10.1039/c39880001301
• 作为产物：
  描述：

  DL-2-O-Benzoyl-3,4,5,6-tetra-O-benzyl-1-deoxy-1-fluoro-scyllo-inositol 在 sodium hydroxide 作用下， 生成 (1S,2R,3R,4S,5R,6S)-2-fluoro-3,4,5,6-tetrakis(phenylmethoxy)cyclohexan-1-ol
  参考文献：
  名称：

  （–）-1L-1-脱氧-1-氟-肌醇的合成；一种潜在的化合物，可用于清除磷脂酰肌醇反应

  摘要：

  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。

  DOI：

  10.1039/c39880001301

文献信息

• Synthesis of 3,4,5,6-tetrakisphosphates of DL-1,2-dideoxy-1,2-difluoro-myo-inositol and DL-1,2-dideoxy-1,2-difluoro-scyllo-inositol as analogues of DL-myo-inositol 3,4,5,6-tetrakisphosphate
  作者：Kevin R. H. Solomons、Sally Freeman、David R. Poyner、Farid Yafai

  DOI：10.1039/p19960001845

  日期：——

  DL-1,2-Dideoxy-1,2-difluoro-myo-inositol was prepared from DL-3,4,5,6-tetra-O-benzyl-myo-inositol in five steps in an overall yield of 36%. The fluoro substituents were introduced with DAST in separate steps by displacement of hydroxy substituents with inversion of stereochemistry. Difluorination could not be achieved in one step because of competing formation of a 1,4-anhydro derivative. DL-1,2-Dideoxy-1,2-difluoro-scyllo-inositol was prepared in 42% overall yield using similar chemistry, with the required inversion of one stereocentre being accomplished by displacement of a tosyl group with caesium propionate. Both difluoroinositol analogues increased the levels of phytic acid (InsP6) in a skeletal muscle cell line. Each compound was tetraphosphorylated with dibenzyl N,N-diisopropylphosphoramidite in the presence of 1H-tetrazole, with subsequent oxidation of the phosphite with MCPBA. The P–OBn groups were removed by H2/Pd–C, and the sodium salts of the tetrakisphosphates of the difluoroinositol analogues were obtained by cation exchange.

  以 DL-3,4,5,6-四-O-苄基肌醇为原料，分五个步骤制备了 DL-1,2-二脱氧-1,2-二氟肌醇，总收率为 36%。氟取代基是用 DAST 通过取代羟基和反转立体化学分步引入的。由于 1,4-脱氢衍生物的竞争生成，二氟化反应无法在一个步骤中完成。使用类似的化学方法制备了 DL-1,2-二脱氧-1,2-二氟-酰基肌醇，总产率为 42%，所需的一个立体中心的反转是通过用丙酸铯置换一个甲苯基来实现的。这两种二氟肌醇类似物都能增加骨骼肌细胞系中植酸（InsP6）的含量。每种化合物都是在 1H 四氮唑存在下用 N,N-二异丙基亚磷酰胺二苄基进行四磷酸化，然后用 MCPBA 氧化亚磷酸酯。用 H2/Pd-C 除去 P-OBn 基团，然后通过阳离子交换获得二氟肌醇类似物的四磷酸盐钠盐。
• Synthesis of 2-deoxy-2-fluorinated inositol-1-0-dodecylphosphonates as inhibitors of glycosyl phosphatidylinositol phospholipase C
  作者：Hai-Xiao Zhai、Ping-Sheng Lei、James C. Morris、Kojo Mensa-Wilmot、T.Y. Shen

  DOI：10.1016/0040-4039(95)01579-5

  日期：1995.10

  Three 2-deoxy-2-fluorinated inositols and their 1-0-dodecylphosphonate derivatives have been synthesized as non-cleavable inhibitors of glycosyl phosphatidylinositol phospholipase C. Their structure-activity relationship is discussed.

  已经合成了三种2-脱氧-2-氟代肌醇及其1-0-十二烷基膦酸酯衍生物作为糖基磷脂酰肌醇磷脂酶C的不可裂解的抑制剂。讨论了它们的结构-活性关系。
• Synthesis of d-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer as analogues of myo-inositol 3,4,5,6-tetrakisphosphate
  作者：Kevin R.H. Solomons、Sally Freeman、Carl H. Schwalbe、Stephen B. Shears、Deborah J. Nelson、Weiwen Xie、Karol S. Bruzik、Marcia A. Kaetzel

  DOI：10.1016/s0008-6215(98)00146-3

  日期：1998.6

  DL-3,4,5,6-Tetra-O-benzyl-1-deoxy-1-fluoro-scyllo-inositol was resolved using (-)-(1S, 4R)-camphanyl chloride. The diastereoisomers formed were separated and the structure of D-3,4,5,6-tetra-O-benzyl-2-(1S,4R)-camphanyl-1-deoxy-1-fluoro-scyllo-inositol was solved by X-ray crystallography to an R-factor of 4.2%. A series of manipulations led to the preparation of 0-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer. The D-1,2-difluoro enantiomer stereospecifically inhibited CaMK II-activated Cl- current, but with low potency; however, efficacy of this compound was greatly enhanced by myo-inositol 3,4,5,6-tetrakisphosphate itself. (C) 1998 Elsevier Science Ltd. All rights reserved.
• General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-Glycerols
  作者：Stephen F. Martin、John A. Josey、Yue-Ling Wong、Daniel W. Dean

  DOI：10.1021/jo00096a023

  日期：1994.8

  An efficient phosphite coupling protocol is described for the syntheses of the major classes of phospholipids that are derived from 1,2-O-diacyl-sn-glycerols and analogues thereof. The symmetrical diacyl glycerols 10c,d were prepared by straightforward acylation of 3-O-benzyl-sn-glycerol (7) with the appropriate carboxylic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). A simple method for preparing saturated and unstaturated mixed 1,2-O-diacyl-sn-glycerols was then devised that involved stepwise acylation of 7 with different alkyl carboxylic acids and debenzylation this procedure is exemplified by the preparation of 10a,b. The 1,2-O-diacyl-sn-glycerols 10a-d were then coupled with suitably protected lipid head groups employing reactive alkyl or aryl dichlorophosphites to give intermediate phosphite triesters in high overall yields. Oxidation or sulfurization of these phosphites proceeded smoothly to give the corresponding phosphate or phosphorothioate triesters, deprotection of which then provided the phosphatidylcholines 16 and 17, the phosphatidylethanolamine 20, the phosphatidylserine 28, and the phosphatidylinositols 37 and 38. Preparation of 37 and 38 required the invention of an improved method for resolving the isopropylidene-protected D-myo-inositol derivative 33. This phosphite coupling procedure was modified to assemble phospholipids bearing-polyunsaturated acyl side chains at the sn-2-position as exemplified by the preparation of the phosphatidylethanolamine 26. The one-pot phosphite coupling procedure is also applicable to the syntheses of a variety of other biologically interesting phospholipid analogues. For example, the phosphatidylinositol analogues 49-51, in which the hydroxyl group at C(2) of the inositol ring has been modified, were prepared in excellent overall yields by conjoining the 1,2-O-diacyl-sn-glycerol 10c with the protected inositol derivatives 44, 45, and 48. Phospholipid analogues that contain other replacements of the phosphate group including phosphoramidates and thiophosphates maybe prepared as evidenced by the syntheses of 56 and 61 in which the sn-3 oxygen atom of the 1,2-O-diacyl-sn-glycerol moiety is replaced with an N-benzyl group or a sulfur atom, respectively.
• Synthesis of fluorodeoxyscylloinositol and phosphatidylfluorodeoxyscylloinositol
  作者：Shu Shu Yang、Thomas R. Beattie、T.Y. Shen

  DOI：10.1016/s0040-4039(00)85882-7

  日期：1982.1