allyl 6-[benzyl-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)]-phosphonato-2,3,4-tri-O-benzyl-α-D-mannopyranoside | 1338476-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 6-[benzyl-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)]-phosphonato-2,3,4-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[phenylmethoxy-[[(2R,3R,4S,5S,6S)-3,4,5-tris(phenylmethoxy)-6-prop-2-enoxyoxan-2-yl]methoxy]phosphoryl]oxyoxan-2-yl]methyl acetate
• CAS: 1338476-73-5
• 化学式: C₅₁H₆₀NO₁₇P
• 分子量: 990.008
• InChiKey: FUHGQUWXBGQUTK-BXURYHAESA-N

物化性质

• 沸点：
  976.1±65.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  70
• 可旋转键数：
  28
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  208
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  allyl 6-[benzyl-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)]-phosphonato-2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[hydroxy-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-propoxyoxan-2-yl]methoxy]phosphoryl]oxyoxan-2-yl]methyl acetate
  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
• 作为产物：
  描述：

  2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 生成 allyl 6-[benzyl-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)]-phosphonato-2,3,4-tri-O-benzyl-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