2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<4,6-di-O-acetyl-2-amino-2-deoxy-3-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-β-D-galactopyranosyl>-β-D-glucopyranoside | 139276-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<4,6-di-O-acetyl-2-amino-2-deoxy-3-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-β-D-galactopyranosyl>-β-D-glucopyranoside
• 英文别名: [(2S,4'S,4aR,5S,5'R,6'R,7R,8R,8aR)-5'-acetamido-4',8-diacetyloxy-5-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-3-oxo-6'-[(1S,2R)-1,2,3-triacetyloxypropyl]spiro[4,4a,5,7,8,8a-hexahydropyrano[4,3-b][1,4]oxazine-2,2'-oxane]-7-yl]methyl acetate
• CAS: 139276-05-4
• 化学式: C₄₆H₆₈N₂O₂₆Si
• 分子量: 1093.13
• InChiKey: IKSIXZCKTIWPEF-HXYFYBRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.67
• 重原子数：
  75.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  350.28
• 氢给体数：
  2.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<4,6-di-O-acetyl-2-amino-2-deoxy-3-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-β-D-galactopyranosyl>-β-D-glucopyranoside 在 1,1-二氯甲醚 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 caesium carbonate 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.5h， 生成 2-<<2-(methoxycarbonyl)ethyl>thio>ethyl 4-O-<2-amino-2-deoxy-3-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-β-D-galactopyranosyl>-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and conformational analysis of GM3 lactam; a hydrolytically stable analog of GM3 ganglioside lactone

  摘要：

  DOI：

  10.1021/ja00032a049
• 作为产物：
  描述：

  乙酸酐 、 2-(trimethylsilyl)ethyl 4-O-<2-amino-2-deoxy-3-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-β-D-galactopyranosyl>-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 以90%的产率得到2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<4,6-di-O-acetyl-2-amino-2-deoxy-3-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-β-D-galactopyranosyl>-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Ganglioside Lactams Corresponding to GM1-, GM2-, GM3-, and GM4-Ganglioside Lactones

  摘要：

  Ganglioside lactams are potentially useful analogs of ganglioside lactones, which are highly immunogenic derivatives of gangliosides. The lactam corresponding to the G(M3)-lactone saccharide has been synthesized by sialylation of a suitably protected lactose derivative carrying an azido group in the 2'-position, followed by reduction and ring closure to form G(M3)-lactam. Glycosylation in the 4-position of the central saccharide unit gave the G(M2)- and G(M1)- lactam saccharides. By a similar route, a 2-azido-Gal derivative was sialylated and treated as above to give the G(M4)-lactam saccharide. Deprotection gave the G(M2-4)-lactam saccharides in water soluble form, whereas attempted deprotection of the G(M1)-lactam caused its degradation. The G(M3)-lactam saccharide was coupled to ceramide, to afford the ganglioside lactam analog, and via a spacer to bovine serum albumin (BSA). The BSA conjugate was used as immunogen to raise monoclonal antibodies that cross-reacted with G(M3)-lactone. The antibodies were used in a histological staining of murine melanoma cells, clearly showing the presence of G(M3)-lactone on the cell surface. Keeping the G(M2-4)-lactam saccharides in D2O at 37 degrees C for 1 month caused marginal (0-11%) hydrolysis of the lactam ring.

  DOI：

  10.1021/ja00122a002