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)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside | 221524-16-9

• 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)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside
• 英文别名: methyl (2R,3S,4R,5S,6R)-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-5-acetyloxy-2-(acetyloxymethyl)-6-[(3R,4S,5R,6S)-4,5-diacetyloxy-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-3-hydroxyoxan-4-yl]oxy-5-(diacetylamino)-3-phenylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 221524-16-9
• 化学式: C₅₂H₇₃NO₂₇SSi
• 分子量: 1204.29
• InChiKey: FJSAKKKNRQWFOK-DBMJKOLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  82
• 可旋转键数：
  33
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  375
• 氢给体数：
  1
• 氢受体数：
  28

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)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside 在 吡啶 作用下， 以97%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)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  一种新型的立体选择性α-唾液酸化供体；α（2-8）连接的双唾液酸单元的高效合成

  摘要：

  新的唾液酸供体甲基5-（N，N-二乙酰基）-4,7,8,9-四-O-乙酰基-2-硫代-3-硫代苯基-2,3,5-三苯氧基-D-赤型通过对相应的5-乙酰氨基化合物1进行N-乙酰化，合成了-L-葡萄糖-2-壬基吡喃糖苷（2）。具有一个或两个未保护的羟基的单糖和二糖苷元的α-唾液酸化以高收率提供了相应的二糖和三糖，并且具有几乎完全的区域选择性和立体选择性。作为一个实例，因此以44％的收率获得了Neu5Acα（2→8）Neu5Ac衍生物。没有观察到相应的β端基异构体。

  DOI：

  10.1016/s0040-4039(99)00175-6
• 作为产物：
  描述：

  Methyl onate 在 甲磺酰溴 、 MS (3 Angstroem) 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 34.5h， 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)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  一种新型的立体选择性α-唾液酸化供体；α（2-8）连接的双唾液酸单元的高效合成

  摘要：

  新的唾液酸供体甲基5-（N，N-二乙酰基）-4,7,8,9-四-O-乙酰基-2-硫代-3-硫代苯基-2,3,5-三苯氧基-D-赤型通过对相应的5-乙酰氨基化合物1进行N-乙酰化，合成了-L-葡萄糖-2-壬基吡喃糖苷（2）。具有一个或两个未保护的羟基的单糖和二糖苷元的α-唾液酸化以高收率提供了相应的二糖和三糖，并且具有几乎完全的区域选择性和立体选择性。作为一个实例，因此以44％的收率获得了Neu5Acα（2→8）Neu5Ac衍生物。没有观察到相应的β端基异构体。

  DOI：

  10.1016/s0040-4039(99)00175-6

文献信息

• Synthesis of GD3-lactam: a potential ligand for the development of an anti-melanoma vaccine
  作者：Nafizal Hossain、Amparo Zapata、Mikael Wilstermann、Ulf J. Nilsson、Göran Magnusson

  DOI：10.1016/s0008-6215(02)00036-8

  日期：2002.4

  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.