α-D-galactopyranosyl β-D-psicofuranoside | 1242059-09-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-galactopyranosyl β-D-psicofuranoside
• 英文别名: Gal(a1-2b)Psif；(2R,3R,4S,5R,6R)-2-[(2S,3R,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1242059-09-1
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: CZMRCDWAGMRECN-SGDZQHEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl β-D-psicofuranoside 在 10% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以100%的产率得到α-D-galactopyranosyl β-D-psicofuranoside
  参考文献：
  名称：

  Chemical synthesis of β-d-psicofuranosyl disaccharides

  摘要：

  Disaccharides composed of a beta-D-psicofuranosyl unit were prepared by the glycosylation reaction of monosaccharide acceptors including three 23,4,6-tetra-O-protected hexopyranoses with a D-psicofuranosyl benzyl phthalate derivative (4). A beta-D-psicofuranosidic bond was formed by the TMSOTf-promoted reaction with high selectivity. Removal of the O-protecting groups from the resulting a-D-hexopyranosyl beta-D-psicofuranosides furnished the first chemical synthesis of alpha-D-gluco-, alpha-D-galacto-, and et-D-mannopyranosyl beta-D-psicofuranosides. The common beta-D-psicofuranosyl donor 4 was derived efficiently from D-psicose in five steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.030