[(2R,3S,4S,5S,6S)-6-[2-[[(2S)-5-amino-1-oxo-1-[3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(phosphonooxymethyl)oxan-2-yl]oxypropylamino]pentan-2-yl]amino]-2-oxoethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl dihydrogen phosphate | 1428872-97-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(2R,3S,4S,5S,6S)-6-[2-[[(2S)-5-amino-1-oxo-1-[3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(phosphonooxymethyl)oxan-2-yl]oxypropylamino]pentan-2-yl]amino]-2-oxoethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl dihydrogen phosphate
• CAS: 1428872-97-2
• 化学式: C₂₂H₄₃N₃O₂₀P₂
• 分子量: 731.539
• InChiKey: KQQJROOGJFLPEZ-KWKIKRANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  376
• 氢给体数：
  13
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以80%的产率得到[(2R,3S,4S,5S,6S)-6-[2-[[(2S)-5-amino-1-oxo-1-[3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(phosphonooxymethyl)oxan-2-yl]oxypropylamino]pentan-2-yl]amino]-2-oxoethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl dihydrogen phosphate
  参考文献：
  名称：

  Synthesis of novel bivalent mimetic ligands for mannose-6-phosphate receptors

  摘要：

  Mannose-6-phosphate (M6P)-containing N-linked glycans are essential signaling molecules for sorting hydrolases in eukaryotic cells. Their receptors, especially the cation-independent M6P receptors (CI-MPRs), have emerged as promising protein targets for targeted drug delivery for the treatment of lysosomal storage disease and liver fibrosis. In this Letter, we describe the design and synthesis of novel bivalent mimetic ligands for CI-MPRs. We report that for the first time, a newly-discovered binding motif, GlcNAc-M6P, has been incorporated in mimetic ligands. M6P- and GlcNAc-M6P-containing building blocks, equipped with NH2 and CO2H handles, have been prepared and assembled with an ornithine linker through amide coupling reactions. Efficient global deprotection protocols have also been developed which have been showcased in the synthesis of our novel bivalent mimetic ligands. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.068