propyl 6-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-phosphonato-1-α-D-mannopyranoside | 1338476-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl 6-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-phosphonato-1-α-D-mannopyranoside
• 英文别名: [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-propoxyoxan-2-yl]methyl hydrogen phosphate
• CAS: 1338476-76-8
• 化学式: C₁₇H₃₂NO₁₄P
• 分子量: 505.413
• InChiKey: PDENJKJEEZRMFD-YKDKKWLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  234
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 在 四氮唑 、 palladium 10% on activated carbon 、 氢气 、 一水合肼 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 46.0h， 生成 propyl 6-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-phosphonato-1-α-D-mannopyranoside
  参考文献：
  名称：

  Chemical Synthesis of N-Linked Glycans Carrying Both Mannose-6-phosphate and GlcNAc-Mannose-6-phosphate Motifs

  摘要：

  Mannose-6-phosphate (M6P) containing N-linked glycans are the essential targeting signals for hydrolases sorting in eukaryotic cells. To facilitate their structural and binding analyses, a highly efficient and convergent method has been developed to prepare complex N-linked glycans with well-defined M6P and N-acetylglucosamine (GlcNAc)-M6P motifs, a newly identified binding element for M6P receptors. The GlcNAc-M6P motif was stereoselectively installed at the late stage of the synthesis. Sequential deprotection of benzyl and acetate groups provided the fully deprotected N-glycans in excellent yield.

  DOI：

  10.1021/jo2010999

文献信息

• Chemical Synthesis of N-Linked Glycans Carrying Both Mannose-6-phosphate and GlcNAc-Mannose-6-phosphate Motifs
  作者：Yunpeng Liu、Gong Chen

  DOI：10.1021/jo2010999

  日期：2011.11.4

  Mannose-6-phosphate (M6P) containing N-linked glycans are the essential targeting signals for hydrolases sorting in eukaryotic cells. To facilitate their structural and binding analyses, a highly efficient and convergent method has been developed to prepare complex N-linked glycans with well-defined M6P and N-acetylglucosamine (GlcNAc)-M6P motifs, a newly identified binding element for M6P receptors. The GlcNAc-M6P motif was stereoselectively installed at the late stage of the synthesis. Sequential deprotection of benzyl and acetate groups provided the fully deprotected N-glycans in excellent yield.