(1R,3S,3aS,6S,6aR)-6-Amino-4-(2,2-dimethyl-propionyloxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-tris-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-2-yloxy]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-carboxylic acid | 566196-38-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,3S,3aS,6S,6aR)-6-Amino-4-(2,2-dimethyl-propionyloxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-tris-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-2-yloxy]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-carboxylic acid
• CAS: 566196-38-1
• 化学式: C₄₀H₆₃NO₁₅
• 分子量: 797.938
• InChiKey: CBGSGXNOWDFPOU-BVNHIJHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  56.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  222.51
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,3aS,6S,6aR)-6-Amino-4-(2,2-dimethyl-propionyloxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-tris-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-2-yloxy]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-carboxylic acid 在 lithium hydroxide 作用下， 以 乙腈 为溶剂， 以85%的产率得到(1R,3S,3aS,6R,6aR)-6-amino-3-β-D-glucopyrannosyl-3,3a,6,6a-tetrahydro-1H-cyclopenta[1,2-c]furan-1-carboxylic acid
  参考文献：
  名称：

  Homochiral rigid γ-amino acid glycosides from aucubin

  摘要：

  Two homochiral glucosylated hydroxy gamma-amino acids 7 and 11 were synthesized by chiral pool synthesis in eight steps from the natural iridoid aucubin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00020-x
• 作为产物：
  描述：

  (1R,3S,3aS,6S,6aR)-4-(2,2-dimethylpropanoyloxymethyl)-6-(1,3-dioxoisoindol-2-yl)-3-[(2S,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)oxan-2-yl]oxy-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-carboxylic acid 在 肼 作用下， 以 乙醇 为溶剂， 以82%的产率得到(1R,3S,3aS,6S,6aR)-6-Amino-4-(2,2-dimethyl-propionyloxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-tris-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-2-yloxy]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-carboxylic acid
  参考文献：
  名称：

  Homochiral rigid γ-amino acid glycosides from aucubin

  摘要：

  Two homochiral glucosylated hydroxy gamma-amino acids 7 and 11 were synthesized by chiral pool synthesis in eight steps from the natural iridoid aucubin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00020-x