(S)-2-Acetylamino-3-((2S,3R,4R,5R,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-N-(3-azido-propyl)-propionamide | 914456-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-Acetylamino-3-((2S,3R,4R,5R,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-N-(3-azido-propyl)-propionamide
• 英文别名: (2S)-2-acetamido-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-N-(3-azidopropyl)propanamide
• CAS: 914456-72-7
• 化学式: C₁₆H₂₈N₆O₈
• 分子量: 432.434
• InChiKey: HBHSFEDIAGLFBL-OTJBPAGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  181
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-2-Acetylamino-3-((2S,3R,4R,5R,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-N-(3-azido-propyl)-propionamide 、 (2S)-2-[[(2S)-2-acetamidopropanoyl]amino]-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxo-6-(pent-4-ynoylamino)hexan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-6-(pent-4-ynoylamino)hexan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-6-(pent-4-ynoylamino)hexanamide 在 phosphate buffered saline 、 铜 作用下， 以 水 为溶剂， 反应 2.0h， 以65%的产率得到
  参考文献：
  名称：

  A Potentially Valuable Advance in the Synthesis of Carbohydrate-Based Anticancer Vaccines through Extended Cycloaddition Chemistry

  摘要：

  An advance in the long-term problem of joining complex oligosaccharides to polypeptides and even proteins is described herein. The key method involves equipping the oligosaccharide sector with an azide and the polypeptide with pendant alkynyl functionality. The two sectors are joined through a "click-like" cycloaddition. The method encompasses oligosaccharide constructs with several azide linkages which undergo concurrent cycloaddition to peptide-based acetylenes. This technology could well prove to be useful in the construction of fully synthetic vaccines.

  DOI：

  10.1021/jo061406i
• 作为产物：
  描述：

  N-芴甲氧羰基-O-BETA-(2-乙酰氨基-2-脱氧-3,4,6-三-O-乙酰基-ALPHA-D-吡喃半乳糖基)-L-丝氨酸 在 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (S)-2-Acetylamino-3-((2S,3R,4R,5R,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-N-(3-azido-propyl)-propionamide
  参考文献：
  名称：

  A Potentially Valuable Advance in the Synthesis of Carbohydrate-Based Anticancer Vaccines through Extended Cycloaddition Chemistry

  摘要：

  An advance in the long-term problem of joining complex oligosaccharides to polypeptides and even proteins is described herein. The key method involves equipping the oligosaccharide sector with an azide and the polypeptide with pendant alkynyl functionality. The two sectors are joined through a "click-like" cycloaddition. The method encompasses oligosaccharide constructs with several azide linkages which undergo concurrent cycloaddition to peptide-based acetylenes. This technology could well prove to be useful in the construction of fully synthetic vaccines.

  DOI：

  10.1021/jo061406i

文献信息

• A Potentially Valuable Advance in the Synthesis of Carbohydrate-Based Anticancer Vaccines through Extended Cycloaddition Chemistry
  作者：Qian Wan、Jiehao Chen、Gong Chen、Samuel J. Danishefsky

  DOI：10.1021/jo061406i

  日期：2006.10.1

  An advance in the long-term problem of joining complex oligosaccharides to polypeptides and even proteins is described herein. The key method involves equipping the oligosaccharide sector with an azide and the polypeptide with pendant alkynyl functionality. The two sectors are joined through a "click-like" cycloaddition. The method encompasses oligosaccharide constructs with several azide linkages which undergo concurrent cycloaddition to peptide-based acetylenes. This technology could well prove to be useful in the construction of fully synthetic vaccines.