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)-2-azido-6-O-benzoyl-2-deoxy-β-D-galactopyranoside | 221524-14-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 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)-2-azido-6-O-benzoyl-2-deoxy-β-D-galactopyranoside
• 英文别名: methyl (2S,3S,4R,5S,6R)-4-acetyloxy-2-[(2R,3R,4R,5R,6R)-5-azido-2-(benzoyloxymethyl)-3-hydroxy-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-5-(diacetylamino)-3-phenylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 221524-14-7
• 化学式: C₄₆H₆₀N₄O₁₉SSi
• 分子量: 1033.15
• InChiKey: HDFBBQDMXJKEBQ-WBLLRLNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  71
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  292
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 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)-2-azido-6-O-benzoyl-2-deoxy-β-D-galactopyranoside 在 吡啶 作用下， 以91%的产率得到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
• 作为产物：
  描述：

  Methyl onate 在 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)-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