benzyl 5-acetamido-3,5-dideoxy-2,4,7,8,9-penta-O-trimethylsilyl-D-glycero-D-galactononulpyranosonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 5-acetamido-3,5-dideoxy-2,4,7,8,9-penta-O-trimethylsilyl-D-glycero-D-galactononulpyranosonate
• 英文别名: benzyl (2R,4S,5S,6R)-5-acetamido-2,4-bis(trimethylsilyloxy)-6-[(1S,2R)-1,2,3-tris(trimethylsilyloxy)propyl]oxane-2-carboxylate
• 化学式: C₃₃H₆₅NO₉Si₅
• 分子量: 760.308
• InChiKey: CXMZXWBLYVDXSX-RPCSGBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl 5-acetamido-3,5-dideoxy-2,4,7,8,9-penta-O-trimethylsilyl-D-glycero-D-galactononulpyranosonate 、 乙酸酐 在 吡啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 0.75h， 以28%的产率得到benzyl 5-acetamido-4-O-acetyl-3,5-dideoxy-2,7,8,9-tetra-O-trimethylsilyl-D-glycero-D-galacto-nonulpyranosonate
  参考文献：
  名称：

  Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology

  摘要：

  Postglycosylation acetylation of sialic acid imparts unique roles to sialoglycoconjugates in mammalian immune response making structural and functional understanding of these analogues important. Five partially O-acetylated Neu5Ac analogues have been synthesized. Reaction of per-O-silylated Neu5Ac ester with AcOH and Ac2O in pyridine promotes regioselective silyl ether/acetate exchange in the following order: C-4 (2 degrees) > C-9 (1 degrees) > C-8 (2 degrees) > C-2 (anomeric). Subsequent hydrogenolysis affords the corresponding sialic acid analogues as useful chemical biology tools.

  DOI：

  10.1021/ol502389g
• 作为产物：
  描述：

  溴甲苯 、 N-acetyl neuraminic acid 在 吡啶 、 potassium carbonate 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 benzyl 5-acetamido-3,5-dideoxy-2,4,7,8,9-penta-O-trimethylsilyl-D-glycero-D-galactononulpyranosonate
  参考文献：
  名称：

  Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology

  摘要：

  Postglycosylation acetylation of sialic acid imparts unique roles to sialoglycoconjugates in mammalian immune response making structural and functional understanding of these analogues important. Five partially O-acetylated Neu5Ac analogues have been synthesized. Reaction of per-O-silylated Neu5Ac ester with AcOH and Ac2O in pyridine promotes regioselective silyl ether/acetate exchange in the following order: C-4 (2 degrees) > C-9 (1 degrees) > C-8 (2 degrees) > C-2 (anomeric). Subsequent hydrogenolysis affords the corresponding sialic acid analogues as useful chemical biology tools.

  DOI：

  10.1021/ol502389g

文献信息

• Synthesis of Partially <i>O-</i>Acetylated <i>N</i>-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology
  作者：Simon S. Park、Jacquelyn Gervay-Hague

  DOI：10.1021/ol502389g

  日期：2014.10.3

  Postglycosylation acetylation of sialic acid imparts unique roles to sialoglycoconjugates in mammalian immune response making structural and functional understanding of these analogues important. Five partially O-acetylated Neu5Ac analogues have been synthesized. Reaction of per-O-silylated Neu5Ac ester with AcOH and Ac2O in pyridine promotes regioselective silyl ether/acetate exchange in the following order: C-4 (2 degrees) > C-9 (1 degrees) > C-8 (2 degrees) > C-2 (anomeric). Subsequent hydrogenolysis affords the corresponding sialic acid analogues as useful chemical biology tools.