Methyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside | 14520-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside
• 英文别名: [(2S,3S,4R,5R)-3,4-diacetyloxy-5-methoxyoxolan-2-yl]methyl acetate
• CAS: 14520-33-3
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: RUSRQHXGPHZZNI-NNYUYHANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙酸酐 、 methyl α-L-arabinofuranoside 在 吡啶 作用下， 生成 Methyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside
  参考文献：
  名称：

  Ito, Teiichiro; Yamai, Mitsuru; Nishio, Toshiyuki, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 3, p. 491 - 498

  摘要：

  DOI：

文献信息

• Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases
  作者：Andrea Bordoni、Rosa M. de Lederkremer、Carla Marino

  DOI：10.1016/j.bmc.2010.05.038

  日期：2010.7

  Derivatives of 5-deoxy-beta-D-galactofuranose (5-deoxy-alpha-L-arabino-hexofuranose) have been synthesized starting from D-galacturonic acid. The synthesis of methyl 5-deoxy-alpha-L-arabino-hexofuranoside (14 alpha) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14 alpha was converted into per-O-acetyl-5-deoxy-alpha,beta-L-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl4-promoted glycosylation of 16 led to 4-nitrophenyl (19 alpha), and 4-methylthiophenyl 5-deoxy-alpha-L-arabino-hexofuranosides (20 alpha). The oxygenated analog 4-methylphenyl 1-thio-beta-D-galactofuranoside (23 beta) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-beta-D-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein. (C) 2010 Elsevier Ltd. All rights reserved.
• US4065616A
  申请人：——

  公开号：US4065616A

  公开（公告）日：1977-12-27