3-C-(α-D-galactofuranosyl)prop-1-ene | 1415315-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-C-(α-D-galactofuranosyl)prop-1-ene
• CAS: 1415315-84-2
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: OGJZAWJMMNGNSL-ZEBDFXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  90.15
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-C-(2,3,5,6-tetra-O-tert-butyldimethylsilyl-α,β-D-galactofuranosyl)prop-1-ene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 3-C-(β-D-galactofuranosyl)prop-1-ene 、 3-C-(α-D-galactofuranosyl)prop-1-ene
  参考文献：
  名称：

  Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor

  摘要：

  The use of the easily available persilylated derivative 1 for the synthesis of C- and S-Galf derivatives has been investigated. By anomeric iodination of 1 with TMSI, followed by in situ coupling with C-and S-nucleophiles under very mild conditions and in the absence of promoters, derivatives with value as glycomimetics or as precursors of glycobiological tools were synthesized. Among them, the synthesis of the isolable 1-galactofuranosylthiol 15 is remarkable, as it paves the way for alternative approaches for S-galactofuranosyl derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.08.021

文献信息

• Switching between <i>X</i>-Pyrano-, <i>X</i>-Furano-, and Anhydro-<i>X</i>-pyranoside Synthesis (X = C, N) under Lewis acid Catalyzed Conditions
  作者：Youngran Seo、Jared M. Lowe、Neyen Romano、Michel R. Gagné

  DOI：10.1021/acs.orglett.1c01713

  日期：2021.8.6

  A variety of C-glycosides can be obtained from the fluoroarylborane (B(C6F5)3) or silylium (R3Si+) catalyzed functionalization of 1-MeO- and per-TMS-sugars with TMS-X reagents. A one-step functionalization with a change as simple as the addition order and/or Lewis acid and TMS-X enables one to afford chiral synthons that are common (C-pyranosides), have few viable synthetic methods (C-furanosides)

  各种C-糖苷可以从氟芳基硼烷(B(C 6 F 5 ) 3 )或硅基(R 3 Si + )催化的1-MeO-和全TMS-糖与TMS-X试剂的官能化获得。一步功能化只需简单地改变加成顺序和/或路易斯酸和 TMS-X，即可获得常见的手性合成子（ C-吡喃糖苷），但几乎没有可行的合成方法（ C-呋喃糖苷），或实际上是未知的（脱水-C-吡喃糖苷），其机械地分别由是否发生直接取代、异构化/取代或取代/异构化而产生。