β-D-galactopyranosyl-(1'->3)-4-aminodeoxy-L-chiro-inositol | 1197003-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl-(1'->3)-4-aminodeoxy-L-chiro-inositol
• 英文别名: (1R,2R,3S,4S,5S,6R)-5-amino-6-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexane-1,2,3,4-tetrol
• CAS: 1197003-15-8
• 化学式: C₁₂H₂₃NO₁₀
• 分子量: 341.315
• InChiKey: NGTHUUQTUCAHNE-ZGROBUEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  206
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  在 Dowex-50 H⁺ resin 作用下， 以 二氯甲烷 为溶剂， 生成 β-D-galactopyranosyl-(1'->3)-4-aminodeoxy-L-chiro-inositol
  参考文献：
  名称：

  Chemoenzymatic synthesis of glycosyl-deoxyinositol derivatives. First example of a fagopyritol β-analogue containing an aminoinositol unit

  摘要：

  The first synthesis of two fagopyritol beta-analogues (beta-D-galactopyranosyl-(1' -> 1)-conduramine F-4 and beta-D-galactopyranosyl-(1' -> 3)-4-aminodeoxy-L-chiro-inositol) has been accomplished by a chemoenzymatic route in satisfactory yields. The key step of the synthesis is the TMSOTf-promoted glycosylation reaction of a deoxyconduritol derivative. The methodology is amenable to scale-up and expandable to the preparation of other pseudofagopyritols. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.011