2-propyl 6-O-acetyl-3-deoxy-4-(R)-(2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl)-4-tio-α-D-threo-hexopyranosid-2-ulose | 1415315-79-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-propyl 6-O-acetyl-3-deoxy-4-(R)-(2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl)-4-tio-α-D-threo-hexopyranosid-2-ulose
• 英文别名: 2-propyl 6-O-acetyl-3-deoxy-4-R-(2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl)-4-tio-α-D-threo-hexopyranosid-2-ulose
• CAS: 1415315-79-5
• 化学式: C₄₁H₈₄O₁₀SSi₄
• 分子量: 881.52
• InChiKey: OLYYCMLVLAYLHH-QEJUJOBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.68
• 重原子数：
  56.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  107.98
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  2,3,5,6-tetra-O-tert-butyldimethylsilyl-1-thio-α,β-D-galactofuranose 、 (2S,6S)-6-acetoxymethyl-2-(2-propyloxy)-2H-pyran-3(6H)-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以35%的产率得到2-propyl 6-O-acetyl-3-deoxy-4-(S)-(2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl)-4-tio-α-D-threo-hexopyranosid-2-ulose
  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