4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-methylsulfanyl-3,5-bis-(4-oxo-pentanoyloxy)-tetrahydro-pyran-4-yl ester | 187330-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-methylsulfanyl-3,5-bis-(4-oxo-pentanoyloxy)-tetrahydro-pyran-4-yl ester
• CAS: 187330-14-9
• 化学式: C₂₉H₃₈O₁₁S
• 分子量: 594.68
• InChiKey: KNMOVWQMIUSFNL-OMNZJWBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  41.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  148.57
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-methylsulfanyl-3,5-bis-(4-oxo-pentanoyloxy)-tetrahydro-pyran-4-yl ester 在 4 A molecular sieve 、 四丁基溴化铵 、 silver trifluoromethanesulfonate 、 三氟乙酸 、 copper(ll) bromide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  A new strategy for stereoselective synthesis of sialic acid-containing glycopeptide fragment

  摘要：

  Sialic acid donor 5, which has a thiophenyl group as a stereocontrolling auxiliary and thiomethyl group as a leaving group was prepared and subjected to model glycosylation. Reactions with acceptor substrates 6, 7, and 8 gave coupled products 9b, 10b, and 11b, respectively, in a higher efficiency than previously observed for the bromide la. This reaction was further applied to the synthesis of protected glyco-amino acid fragment 12, that is strategically designed for the synthesis of sialic acid containing glycopeptides. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00172-1
• 作为产物：
  描述：

  乙酰丙酸酐 、 (2R,3R,4S,5R,6S)-2-Benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3,4,5-triol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 以84%的产率得到4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-methylsulfanyl-3,5-bis-(4-oxo-pentanoyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  A new strategy for stereoselective synthesis of sialic acid-containing glycopeptide fragment

  摘要：

  Sialic acid donor 5, which has a thiophenyl group as a stereocontrolling auxiliary and thiomethyl group as a leaving group was prepared and subjected to model glycosylation. Reactions with acceptor substrates 6, 7, and 8 gave coupled products 9b, 10b, and 11b, respectively, in a higher efficiency than previously observed for the bromide la. This reaction was further applied to the synthesis of protected glyco-amino acid fragment 12, that is strategically designed for the synthesis of sialic acid containing glycopeptides. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00172-1