6-deoxy-6-C-ethenyl-1,2,3,4-di-O-isopropylidene-5-O-pivaloyl-D-myo-inositol | 904309-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-6-C-ethenyl-1,2,3,4-di-O-isopropylidene-5-O-pivaloyl-D-myo-inositol
• 英文别名: [(1S,2S,6S,7R,8S,9S)-8-ethenyl-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-yl] 2,2-dimethylpropanoate
• CAS: 904309-97-3
• 化学式: C₁₉H₃₀O₆
• 分子量: 354.444
• InChiKey: LXJRUCMLPDSBTR-SPJHXALWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-deoxy-6-C-ethenyl-1,2,3,4-di-O-isopropylidene-5-O-pivaloyl-D-myo-inositol 、 乙酸酐 在 二异丁基氢化铝 、 盐酸 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 甲醇 、 乙酸乙酯 为溶剂， 反应 15.0h， 以86%的产率得到1,2,3,4,5-penta-O-acetyl-6-deoxy-6-C-ethenyl-D-myo-inositol
  参考文献：
  名称：

  A de novo approach to C-branched inositols: synthesis of a myo-inositol precursor for C-linked glycosyl phosphatidylinositols

  摘要：

  C-Linked glycosyl inositols are valuable structure-activity probes because of their greater hydrolytic stability and different conformational behavior compared with their parent O-glycosides. Simple C-branched inositols are synthetic precursors to these and other groups of inositol mimetics. Herein is described a de novo synthesis of C-branched inositols that contain a versatile ethenyl side chain for elaboration into more complex appendages. The approach centers on a stereoselective oxocarbenium ion-allylsilane cyclization and provides C-branched inositols with different stereochemical motifs. The synthesis of C-ethenyl-di-O-isopropylidene-myo-, neo-, epi-, and allo-inositols is discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.026
• 作为产物：
  描述：

  5,6-dideoxy-1,2-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 臭氧 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 34.25h， 生成 6-deoxy-6-C-ethenyl-1,2,3,4-di-O-isopropylidene-5-O-pivaloyl-D-myo-inositol
  参考文献：
  名称：

  A de novo approach to C-branched inositols: synthesis of a myo-inositol precursor for C-linked glycosyl phosphatidylinositols

  摘要：

  C-Linked glycosyl inositols are valuable structure-activity probes because of their greater hydrolytic stability and different conformational behavior compared with their parent O-glycosides. Simple C-branched inositols are synthetic precursors to these and other groups of inositol mimetics. Herein is described a de novo synthesis of C-branched inositols that contain a versatile ethenyl side chain for elaboration into more complex appendages. The approach centers on a stereoselective oxocarbenium ion-allylsilane cyclization and provides C-branched inositols with different stereochemical motifs. The synthesis of C-ethenyl-di-O-isopropylidene-myo-, neo-, epi-, and allo-inositols is discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.026