pyrimidin-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside | 215794-87-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pyrimidin-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside
• CAS: 215794-87-9
• 化学式: C₃₈H₃₈N₂O₅S
• 分子量: 634.796
• InChiKey: LAIHYQVREFPNIA-GDWCTEMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.27
• 重原子数：
  46.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.93
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  pyrimidin-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 、 双丙酮葡萄糖 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到
  参考文献：
  名称：

  Synthesis and glycosylation of pyrimidin-2-yl 1-thio-α-d-manno- and -α-l-rhamnopyranoside

  摘要：

  Pyrimidin-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-alpha-D-mannopyrano side (9), pyrimidin-2-yl 2,3,4-tri-O-benzyl-alpha-L-rhamnopyranoside (10), pyrimidin-2-yl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-alpha-D-mannopyranoside (7), and pyrimidin-2-y1 2-O-acetyl-3,4-di-O-benzyl-1-thio-alpha-L-rhamnopyranoside (8) were prepared almost quantitatively fi om the corresponding protected 1,2-O-methoxyethylidene-beta-D-manno-or-beta-L-rhamnopyranose with 2-mercaptopyrimidine in the presence of mercuric bromide. Coupling reactions of the thioglycosides promoted by silver triflate with suitable glycosyl accepters afforded 1,2-trans linked disaccharides. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00164-5
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 在 sodium methylate 、 sodium hydride 、 mercury dibromide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 、 paraffin 为溶剂， 反应 8.5h， 生成 pyrimidin-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and glycosylation of pyrimidin-2-yl 1-thio-α-d-manno- and -α-l-rhamnopyranoside

  摘要：

  Pyrimidin-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-alpha-D-mannopyrano side (9), pyrimidin-2-yl 2,3,4-tri-O-benzyl-alpha-L-rhamnopyranoside (10), pyrimidin-2-yl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-alpha-D-mannopyranoside (7), and pyrimidin-2-y1 2-O-acetyl-3,4-di-O-benzyl-1-thio-alpha-L-rhamnopyranoside (8) were prepared almost quantitatively fi om the corresponding protected 1,2-O-methoxyethylidene-beta-D-manno-or-beta-L-rhamnopyranose with 2-mercaptopyrimidine in the presence of mercuric bromide. Coupling reactions of the thioglycosides promoted by silver triflate with suitable glycosyl accepters afforded 1,2-trans linked disaccharides. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00164-5