β-D-galactopyranosyl-(1'->1)-6-amino-cyclohex-4-ene-2,3-diol | 1197003-13-6

• 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'->1)-6-amino-cyclohex-4-ene-2,3-diol
• 英文别名: (2R,3R,4S,5R,6R)-2-[(1R,2S,5R,6R)-2-amino-5,6-dihydroxycyclohex-3-en-1-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1197003-13-6
• 化学式: C₁₂H₂₁NO₈
• 分子量: 307.301
• InChiKey: SCNWYFBHRPSDCY-JVCRWLNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  166
• 氢给体数：
  7
• 氢受体数：
  9

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'->1)-6-amino-cyclohex-4-ene-2,3-diol
  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