5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal | 904310-22-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal
• 英文别名: (4R,5S)-4-[(4R,5R)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]-5-ethenyl-2,2-dimethyl-1,3-dioxolane
• CAS: 904310-22-1
• 化学式: C₁₈H₂₄O₄S
• 分子量: 336.452
• InChiKey: LPEFTDVZVYTJRQ-ZJIFWQFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 臭氧 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (E)-1-((4R,5S,4'R,5'R)-2,2,2',2'-Tetramethyl-5'-phenylsulfanyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-4-trimethylsilanyl-but-2-en-1-ol
  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：

  (S)-1-((4R,5R)-2,2-Dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-prop-2-en-1-ol 在 偶氮二甲酸二异丙酯 、 camphor-10-sulfonic acid 、 臭氧 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-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