phenyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-galactopyranoside | 260976-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-galactopyranoside
• CAS: 260976-50-9
• 化学式: C₃₃H₃₃N₃O₄S
• 分子量: 567.709
• InChiKey: PEQGULWROBTVGB-CYEGLCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.57
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-galactopyranoside 、 2-(trimethylsilyl)ethyl (2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 3.5h， 以88%的产率得到2-(trimethylsilyl)ethyl (6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of selected aminodeoxy analogues of galabiose and globotriose

  摘要：

  Six aminodeoxy 2-(trimethylsilyl)ethyl (Me3SiEt) glycoside analogues of galabiose (4'- and 6'-aminodeoxy) and globotriose (6 "-, 4 "-, 2 "-, and 6'-aminodeoxy) were synthesized by glycosylation of protected Me3SiEt galactoside and lactoside accepters with azido-substituted monosaccharide donors, followed by reduction of the azido groups and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00229-3
• 作为产物：
  描述：

  phenyl 1-thio-6-O-p-toluenesulfonyl-β-D-galactopyranoside 在 sodium azide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 phenyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of selected aminodeoxy analogues of galabiose and globotriose

  摘要：

  Six aminodeoxy 2-(trimethylsilyl)ethyl (Me3SiEt) glycoside analogues of galabiose (4'- and 6'-aminodeoxy) and globotriose (6 "-, 4 "-, 2 "-, and 6'-aminodeoxy) were synthesized by glycosylation of protected Me3SiEt galactoside and lactoside accepters with azido-substituted monosaccharide donors, followed by reduction of the azido groups and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00229-3