2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2-amino-6-O-benzyl-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 | 151651-17-1

• 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-benzyl-4-O-<2-amino-6-O-benzyl-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
• CAS: 151651-17-1
• 化学式: C₆₄H₈₂N₂O₂₁Si
• 分子量: 1243.44
• InChiKey: LUIHUXSFOUWJEK-WTALYBKWSA-N

物化性质

• 沸点：
  1137.8±65.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  88.0
• 可旋转键数：
  28.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  275.93
• 氢给体数：
  3.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2-amino-6-O-benzyl-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 、 methyl 6-O-acetyl-2-deoxy-3,4-O-isopropylidene-2-phthalimido-1-thio-β-D-galactopyranoside 在 甲磺酰溴 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 生成
  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
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2-azido-6-O-benzyl-2-deoxy-3-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylate)-β-D-galactopyranosyl>-β-D-glucopyranoside 在 吡啶 、 硫化氢 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以70%的产率得到2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2-amino-6-O-benzyl-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