2-(trimethylsilyl)ethyl 4-O-acetyl-2-azido-6-O-benzoyl-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-galactopyranoside | 151651-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 4-O-acetyl-2-azido-6-O-benzoyl-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-galactopyranoside
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3R,4R,5R,6R)-3-acetyloxy-5-azido-2-(benzoyloxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 151651-24-0
• 化学式: C₄₀H₅₆N₄O₁₉Si
• 分子量: 924.986
• InChiKey: UKOZXUDBEDHUOY-BZIGJOKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  64
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  265
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 4-O-acetyl-2-azido-6-O-benzoyl-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-galactopyranoside 在 sodium hydroxide 、 sodium methylate 作用下， 生成 2-(trimethylsilyl)ethyl 2-azido-2-deoxy-3-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-β-D-galactopyranoside
  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：

  O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate 、 Benzoic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-azido-4-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethyl ester 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 一氯化碘 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.5h， 以46%的产率得到2-(trimethylsilyl)ethyl 4-O-acetyl-2-azido-6-O-benzoyl-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-galactopyranoside
  参考文献：
  名称：

  一氯化碘/三氟甲磺酸银（ICI / AgOTf）作为O-糖苷合成的便利促进剂系统。

  摘要：

  用各种硫代糖苷供体和糖受体评估了新型的启动子系统一氯化碘/三氟甲磺酸银（IC1 / AgOTf），并以46-82％的产率获得了O-糖苷。观察到了ICl / AgOTf系统相对于已知启动子系统的一些实际优点，例如方便的试剂处理和不存在与N-琥珀酰亚胺有关的副产物。

  DOI：

  10.1021/ol015547c