1-O-tert-butyl 4-O-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl] (2S)-2-[[(2S)-4-[[(2R,3R,4S,5S,6R)-6-ethylsulfanyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoyl]amino]butanedioate | 229160-30-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-O-tert-butyl 4-O-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl] (2S)-2-[[(2S)-4-[[(2R,3R,4S,5S,6R)-6-ethylsulfanyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoyl]amino]butanedioate
• CAS: 229160-30-9
• 化学式: C₆₃H₇₄N₂O₁₈S
• 分子量: 1179.35
• InChiKey: UBOSMQTXZAULLY-SFAAEXPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  84
• 可旋转键数：
  31
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  288
• 氢给体数：
  5
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyl 4-O-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl] (2S)-2-[[(2S)-4-[[(2R,3R,4S,5S,6R)-6-ethylsulfanyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoyl]amino]butanedioate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以13%的产率得到(1S,3S,4S,5S,6R,7R,12S,15S,20R,22S,23S,24S)-4,5,6-Tris-benzyloxy-12-(9H-fluoren-9-ylmethoxycarbonylamino)-23,24-dihydroxy-22-methoxy-10,13,17-trioxo-2,9,18,21,25-pentaoxa-14-aza-tricyclo[18.2.2.1^3,7]pentacosane-15-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Peptide templated glycosidic bond formation: a new strategy for oligosaccharide synthesis†

  摘要：

  在糖基供体和共价连接到肽模板的受体之间进行的糖基化反应产生了更高的区域和立体选择性，这取决于肽的性质，并且可以通过简单的分子建模来合理化。

  DOI：

  10.1039/a901916b
• 作为产物：
  描述：

  methyl-6-O-carboxy-(N-(9-fluorenylmethoxycarbonyl)-L-aspartic acid-α-tert-butyl ester)-α-D-manno-pyranoside 在 哌啶 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.5h， 生成 1-O-tert-butyl 4-O-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl] (2S)-2-[[(2S)-4-[[(2R,3R,4S,5S,6R)-6-ethylsulfanyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoyl]amino]butanedioate
  参考文献：
  名称：

  Peptide templated glycosylation reactions

  摘要：

  Glycosyl donors and accepters may be covalently linked to aspartic acid residues via OH-6 esters. Peptide elaboration allows glycosylation reactions to be performed between donors and accepters linked to this peptide template. These reactions display increased regio- and stereoselectivities, which are dependent on the nature of the peptide. Simple molecular modelling is used to rationalise the differing product distributions obtained by variation of the linking amino acid sequence. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00494-2

文献信息

• Peptide templated glycosylation reactions
  作者：Richard J Tennant-Eyles、Benjamin G Davis、Antony J Fairbanks

  DOI：10.1016/s0957-4166(99)00494-2

  日期：2000.1

  Glycosyl donors and accepters may be covalently linked to aspartic acid residues via OH-6 esters. Peptide elaboration allows glycosylation reactions to be performed between donors and accepters linked to this peptide template. These reactions display increased regio- and stereoselectivities, which are dependent on the nature of the peptide. Simple molecular modelling is used to rationalise the differing product distributions obtained by variation of the linking amino acid sequence. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Peptide templated glycosidic bond formation: a new strategy for oligosaccharide synthesis†
  作者：Richard J. Tennant-Eyles、Antony J. Fairbanks、Benjamin G. Davis

  DOI：10.1039/a901916b

  日期：——

  Glycosidation reactions performed between glycosyl donors and acceptors covalently linked to a peptide template produced increased regio- and stereo-selectivities, which were dependent on the nature of the peptide, and which may be rationalised by simple molecular modelling.

  在糖基供体和共价连接到肽模板的受体之间进行的糖基化反应产生了更高的区域和立体选择性，这取决于肽的性质，并且可以通过简单的分子建模来合理化。