| 63000-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• CAS: 63000-70-4
• 化学式: C₂₀H₂₀INO₉
• 分子量: 545.285
• InChiKey: YCXQBFIPZOPXPP-ZKXLYKBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  125.51
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2-(5-hydroxyl-4H-pyran-4-one)-methyl-2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient synthesis of thioglycosylated kojic acid bys-glycosyl isothiouronium salts

  摘要：

  In this study, 7-S-glycosides of kojic acid were designed and synthesized as mimics of its 7-O-glycosides to improve its water solubility and metabolic stability. To achieve this synthesis, a one-pot approach involving S-glycosyl isothiouronium salts generated in situ as key intermediates was developed by using 7-chloro-kojic acid as the alkylation reagent. A series of water soluble 7-S-glycosides of kojic acid, incorporating monosaccharides and disaccharides, were prepared using this protocol. Thus, this work offers a mild, convenient, and efficient approach for the synthesis of 7-S-glycosides of kojic acid in medium to good yields.[GRAPHICS].

  DOI：

  10.1080/07328303.2016.1261881
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 在 三乙基硅烷 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  Efficient synthesis of thioglycosylated kojic acid bys-glycosyl isothiouronium salts

  摘要：

  In this study, 7-S-glycosides of kojic acid were designed and synthesized as mimics of its 7-O-glycosides to improve its water solubility and metabolic stability. To achieve this synthesis, a one-pot approach involving S-glycosyl isothiouronium salts generated in situ as key intermediates was developed by using 7-chloro-kojic acid as the alkylation reagent. A series of water soluble 7-S-glycosides of kojic acid, incorporating monosaccharides and disaccharides, were prepared using this protocol. Thus, this work offers a mild, convenient, and efficient approach for the synthesis of 7-S-glycosides of kojic acid in medium to good yields.[GRAPHICS].

  DOI：

  10.1080/07328303.2016.1261881

文献信息

• Novel Approaches for the Synthesis and Activation of Thio- and Selenoglycoside Donors
  作者：Silvia Valerio、Alfonso Iadonisi、Matteo Adinolfi、Alessandra Ravidà

  DOI：10.1021/jo070670o

  日期：2007.8.1

  Alkyl thio-, phenyl seleno-, and phenyl thioglycosides can be prepared through short synthetic sequences based on the generation of glycosyl iodides as versatile intermediates. In addition, a novel cheap combined system (stoichiometric NBS and catalytic Bi(OTf)(3)) has been developed for rapid and efficient activation of a wide variety of thio- and selenoglycoside donors.
• An Efficient Modular Approach for the Assembly of <i>S</i>-Linked Glycopeptoids
  作者：Daniela Comegna、Francesco De Riccardis

  DOI：10.1021/ol901524k

  日期：2009.9.3

  A short and convenient methodology for the synthesis of S-glycosylated peptoid models Is described. The thioglycosylated building blocks were prepared from proper peracetylated sugars via glycosyl iodides in a one-pot fashion and directly employed in a submonomer solidphase stategy.