(S)-1-((4R,5R)-2,2-Dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-prop-2-en-1-ol | 904310-57-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (S)-1-((4R,5R)-2,2-Dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-prop-2-en-1-ol
• CAS: 904310-57-2
• 化学式: C₁₄H₁₈O₃S
• 分子量: 266.361
• InChiKey: YQYWPIMJXPXNBL-YNEHKIRRSA-N

物化性质

• 沸点：
  385.0±42.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (S)-1-((4R,5R)-2,2-Dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-prop-2-en-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 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 8.0h， 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：

  3-O-acetyl-4,5-dideoxy-1,2-O-isopropylidene-4-eno-L-threo-pentose-S-phenyl-monothiohemiacetal 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到(S)-1-((4R,5R)-2,2-Dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-prop-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