(2S,4S,5R,6R)-4-acetyloxy-5-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methoxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid | 202333-93-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6R)-4-acetyloxy-5-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methoxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid
• CAS: 202333-93-5
• 化学式: C₃₃H₃₇NO₁₄
• 分子量: 671.655
• InChiKey: DSCAPEYGYZSUQR-LKHPHCFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-4-acetyloxy-5-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methoxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid 、 6-氨基己酸 在 4-(2',4'-dimethoxyphenyl-Fmoc-aminomethyl)-phenoxy resin 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 一水合肼 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 生成 (2S,4S,5R,6R)-5-Amino-4-hydroxy-2-methoxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid (5-carbamoyl-pentyl)-amide 、 (2S,4S,5R,6R)-5-amino-N-[(2R,3R,4S,6S)-6-[(6-amino-6-oxohexyl)carbamoyl]-4-hydroxy-6-methoxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxamide 、 (2S,4S,5R,6R)-5-amino-N-[(2R,3R,4S,6S)-6-[[(2R,3R,4S,6S)-6-[[(2R,3R,4S,6S)-6-[[(2R,3R,4S,6S)-6-[[(2R,3R,4S,6S)-6-[[(2R,3R,4S,6S)-6-[[(2R,3R,4S,6S)-6-[(6-amino-6-oxohexyl)carbamoyl]-4-hydroxy-6-methoxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]carbamoyl]-4-hydroxy-6-methoxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]carbamoyl]-4-hydroxy-6-methoxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]carbamoyl]-4-hydroxy-6-methoxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]carbamoyl]-4-hydroxy-6-methoxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]carbamoyl]-4-hydroxy-6-methoxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]carbamoyl]-4-hydroxy-6-methoxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxamide 、 (2S,4S,5R,6R)-5-amino-N-[(2R,3R,4S,6S)-6-[[(2R,3R,4S,6S)-6-[(6-amino-6-oxohexyl)carbamoyl]-4-hydroxy-6-methoxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]carbamoyl]-4-hydroxy-6-methoxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxamide
  参考文献：
  名称：

  Solid Phase Synthesis and Secondary Structural Studies of (1→5) Amide-Linked Sialooligomers¹

  摘要：

  A series of dimeric through octameric (1-->5) amid-linked sialooligomers were prepared using solid-phase peptide methods on Rink resin with Fmoc protecting group chemistry. The oligomers were conjugated to epsilon-amino caproic acid in order to model membrane-bound conformations. The secondary structure of the oliogomers was probed with NH/ND exchange rates determined by NMR, and with circular dichroism. The combined structural studies show that a tetramer is required for ordered secondary structure, and that secondary structure is stabilized upon elongation to pentameric and hexameric species. Interestingly, the heptamer shows rapid NH/ND exchange rates; however, ordered secondary structure is restored in the octamer. These studies provide the first evidence that oligomers composed of constrained carbohydrate-derived amino acids form stable secondary structures in water.

  DOI：

  10.1021/jo971415e
• 作为产物：
  描述：

  beta-神经氨酸甲酯 在 吡啶 、 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 44.0h， 生成 (2S,4S,5R,6R)-4-acetyloxy-5-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methoxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  Solid Phase Synthesis and Secondary Structural Studies of (1→5) Amide-Linked Sialooligomers¹

  摘要：

  A series of dimeric through octameric (1-->5) amid-linked sialooligomers were prepared using solid-phase peptide methods on Rink resin with Fmoc protecting group chemistry. The oligomers were conjugated to epsilon-amino caproic acid in order to model membrane-bound conformations. The secondary structure of the oliogomers was probed with NH/ND exchange rates determined by NMR, and with circular dichroism. The combined structural studies show that a tetramer is required for ordered secondary structure, and that secondary structure is stabilized upon elongation to pentameric and hexameric species. Interestingly, the heptamer shows rapid NH/ND exchange rates; however, ordered secondary structure is restored in the octamer. These studies provide the first evidence that oligomers composed of constrained carbohydrate-derived amino acids form stable secondary structures in water.

  DOI：

  10.1021/jo971415e