pyrimidin-2-yl 2,6-di-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside | 215794-95-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: pyrimidin-2-yl 2,6-di-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside
• CAS: 215794-95-9
• 化学式: C₂₈H₃₀N₂O₇S
• 分子量: 538.621
• InChiKey: BCAINONXRZWTOI-IONQDRQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  106.07
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ((2R,3R,4S,5S,6S)-3,4,5-三(苄氧基)-6-甲氧基四氢-2H-吡喃-2-基)甲醇 、 pyrimidin-2-yl 2,6-di-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-(2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-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
• 作为产物：
  描述：

  3,4,6-三-O-苄基-beta-D-吡喃甘露糖-1,2-(甲基原乙酸酯) 在 三氟甲磺酸三甲基硅酯 、 mercury dibromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 pyrimidin-2-yl 2,6-di-O-acetyl-3,4-di-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