| 187330-21-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• CAS: 187330-21-8
• 化学式: C₅₅H₆₄N₄O₂₀
• 分子量: 1101.13
• InChiKey: XSKVQRQGZIASEA-OJUPEZPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  79.0
• 可旋转键数：
  29.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  330.11
• 氢给体数：
  3.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  benzyl (2R,3S,4R,5S,6R)-5-acetamido-2-methylsulfanyl-4-phenylmethoxy-3-phenylsulfanyl-6-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]oxane-2-carboxylate 、 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 以70%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-[O-[benzyl(5acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthioo-D-erythro-α-L-gluco-2-nonulopyranosyl)onate]-(1->6)-O-[(6-O-benzyl-2,3,4-tri-O-levulinoyl-β-Dgalactopyranosyl)-(1->3)]-O-(2-azido-3-O-chloroace...)
  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：

  allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine 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