6,7,8-trideoxy-1,2,3,4-di-O-isopropylidene-5-O-pivaloyl-8-trimethylsilyl-6(E)-eno-L-talo-octose-S-phenyl-monothiohemiacetal | 904310-43-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6,7,8-trideoxy-1,2,3,4-di-O-isopropylidene-5-O-pivaloyl-8-trimethylsilyl-6(E)-eno-L-talo-octose-S-phenyl-monothiohemiacetal
• CAS: 904310-43-6
• 化学式: C₂₈H₄₄O₆SSi
• 分子量: 536.805
• InChiKey: WQOAGOMWUIIAHG-WMVGVGJDSA-N

反应信息

• 作为反应物：
  描述：

  6,7,8-trideoxy-1,2,3,4-di-O-isopropylidene-5-O-pivaloyl-8-trimethylsilyl-6(E)-eno-L-talo-octose-S-phenyl-monothiohemiacetal 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 33.25h， 生成 1,2,3,4,5-penta-O-acetyl-5-deoxy-6-C-ethenyl-D-allo-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-D-ribo-hexose-S-phenyl-monothiohemiacetal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 、 4-二甲氨基吡啶 、 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 16.0h， 生成 6,7,8-trideoxy-1,2,3,4-di-O-isopropylidene-5-O-pivaloyl-8-trimethylsilyl-6(E)-eno-L-talo-octose-S-phenyl-monothiohemiacetal
  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