(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((2R,3S,4S,5R,6S)-4,5-bis-benzoyloxy-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-2-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 848915-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((2R,3S,4S,5R,6S)-4,5-bis-benzoyloxy-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-2-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 848915-03-7
• 化学式: C₄₂H₅₁NO₁₉S
• 分子量: 905.928
• InChiKey: BXTKDNHDXYKQOX-DWHQLYGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  63.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  261.12
• 氢给体数：
  2.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((2R,3S,4S,5R,6S)-4,5-bis-benzoyloxy-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-2-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 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， 反应 2.0h， 以70%的产率得到methyl (4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-3-hydroxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Thiomidoyl approach to the synthesis of α-sialosides

  摘要：

  Novel sialosyl donors, S-benzoxazolyl (SBox) and S-thiazolyl (STaz) sialosides, have been synthesized and applied to the stereoselective synthesis of alpha-sialosides. It was also demonstrated that it is possible to selectively activate SBox sialyl donor over ethyl thioglycoside, allowing the direct synthesis of disaccharide donors that could be used in subsequent glycosylations without further manipulations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.043
• 作为产物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 18-冠醚-6 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 40.0h， 生成 (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((2R,3S,4S,5R,6S)-4,5-bis-benzoyloxy-6-ethylsulfanyl-3-hydroxy-tetrahydro-pyran-2-ylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Thiomidoyl approach to the synthesis of α-sialosides

  摘要：

  Novel sialosyl donors, S-benzoxazolyl (SBox) and S-thiazolyl (STaz) sialosides, have been synthesized and applied to the stereoselective synthesis of alpha-sialosides. It was also demonstrated that it is possible to selectively activate SBox sialyl donor over ethyl thioglycoside, allowing the direct synthesis of disaccharide donors that could be used in subsequent glycosylations without further manipulations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.043