2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-non-2-ulopyranosylonate)-(2->3)-4-O-acetyl-2-azido-6-O-benzoyl-2-deoxy-β-D-galactopyranoside | 221524-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-non-2-ulopyranosylonate)-(2->3)-4-O-acetyl-2-azido-6-O-benzoyl-2-deoxy-β-D-galactopyranoside
• 英文别名: methyl (2R,3S,4R,5S,6R)-4-acetyloxy-2-[(2R,3R,4R,5R,6R)-3-acetyloxy-5-azido-2-(benzoyloxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-5-(diacetylamino)-3-phenylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 221524-15-8
• 化学式: C₄₈H₆₂N₄O₂₀SSi
• 分子量: 1075.19
• InChiKey: GQOLAUBJESKAQL-ZTPPSJIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  74
• 可旋转键数：
  29
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  298
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  氯 2,3,4,6-四-O-苄基-|á-D-吡喃葡萄糖苷 、 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-non-2-ulopyranosylonate)-(2->3)-4-O-acetyl-2-azido-6-O-benzoyl-2-deoxy-β-D-galactopyranoside 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 以83%的产率得到methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside
  参考文献：
  名称：

  三氟甲磺酸铜（II）在三氟化苯中促进的未确定底物的糖基化反应

  摘要：

  描述了由三氟甲磺酸铜（II）诱导的糖基化反应。使用苯并三氟化物作为反应溶剂，将五种糖基供体，葡糖酰氯，氟化物，三氯乙酰亚胺酸酯，1-O-乙酰基化合物和内酯活化，得到相应的葡糖苷。

  DOI：

  10.1016/s0008-6215(02)00029-0
• 作为产物：
  描述：

  Methyl onate 在 吡啶 、 甲磺酰溴 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-non-2-ulopyranosylonate)-(2->3)-4-O-acetyl-2-azido-6-O-benzoyl-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of GD3-lactam: a potential ligand for the development of an anti-melanoma vaccine

  摘要：

  The novel sialyl donor methyl (ethyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-2-thio-3-thiophenyl-D-erthro-beta-L-gluco-non-2-ulopyranosid)onate was used for glycosylation of a lactosyl acceptor to give the GM3-trisaccharide derivative in 83% yield. Introduction of an azido group at C-9" of the GM3-trisaccharide derivative, transformation into a glycosyl acceptor, and sialylation with the above mentioned novel sialyl donor gave a GD3-trisaccharide in 50% yield. Reduction of the azido group gave the corresponding amine, which underwent spontaneous lactamization to the GD3-[1'''-9"]-lactam in an overall yield of 86%. Removal of protecting groups of over five steps, followed by per-O-acetylation gave an acetylated GD3-[1'''-9"]-lactam TMSEt glycoside in 27% overall yield. The acetylated GD3-[1'''-9"]-lactam TMSEt glycoside is suitable for glycosylation of linker-arms and the resulting linker-glycosides are planned to be coupled to carrier proteins. thus providing immunogens for trial vaccinations against malignant melanoma. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00036-8