A First Total Synthesis of Ganglioside HLG-2

Iwayama Y; Ando H; Ishida H; Kiso M

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A First Total Synthesis of Ganglioside HLG-2

机译：神经节苷脂HLG-2的首次全合成

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A first synthesis of the neuritegenic ganglioside HLG-2, which was identified in extracts of the sea cucumber Holothuria leucospilota, is described. The characteristic sequence of the trisaccharide part, alpha-N-glycolylsialyl-(2,4)-alpha-N-acetylsialyl-(2,6)-glucoside, was efficiently assembled by coupling of it highly active N-2,2,2-trichloroethoxycarbonyl (Troc)-protected sialyl donor and a 1,5-lactamized sialyl acceptor with high stereoselectivity. The corresponding trisaccharyl imidate donor was directly glycosidated with the primary hydroxyl group of the ceramide part, producing protected HLG-2 in relatively high yield, global deprotection of which furnished ganglioside HLG-2 in highly pure form.

机译：描述了在海参Holothuria leucospilota提取物中鉴定出的神经突神经节苷脂HLG-2的首次合成。通过将三糖部分的高活性N-2,2,2偶联起来，可以有效地组装三糖部分的特征序列，即α-N-乙醇酰基唾液酸-（2,4）-α-N-乙酰唾液酸基-（2,6）-葡萄糖苷-三氯乙氧羰基（Troc）保护的唾液酸供体和1,5-内酰胺化的唾液酸受体具有高立体选择性。相应的三糖基亚氨酸酯供体直接与神经酰胺部分的伯羟基糖基化，以相对高的产率产生被保护的HLG-2，其整体脱保护提供了高纯度形式的神经节苷脂HLG-2。

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《Chemistry: A European journal》 |2009年第18期|共12页
作者
Iwayama Y; Ando H; Ishida H; Kiso M;
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正文语种 eng
中图分类应用化学;
关键词
gangliosides; glycolipids; natural products; sialic acids; total synthesis;

机译：神经节苷脂;糖脂;天然产物;唾液酸;总合成;

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1. A First Total Synthesis of Ganglioside HLG-2 [J] . Iwayama Y, Ando H, Ishida H, Chemistry: A European journal . 2009,第18期

机译：神经节苷脂HLG-2的首次全合成
2. Efficiently Synthesizing Lacto-Ganglio-Series Gangliosides by Using a Glucosyl Ceramide Cassette Approach: The Total Synthesis of Ganglioside X2 [J] . Shinya Nakashima, Hiromune Ando, Risa Saito, Chemistry, an Asian journal . 2012,第5期

机译：通过使用糖基神经酰胺盒法有效合成Lacto-Ganglio系列神经节苷脂：神经节苷脂X2的总合成
3. Efficiently Synthesizing Lacto-Ganglio-Series Gangliosides by Using a Glucosyl Ceramide Cassette Approach: The Total Synthesis of Ganglioside X2 [J] . Shinya Nakashima, Hiromune Ando, Risa Saito, Chemistry, an Asian journal . 2012,第5期

机译：通过使用葡萄糖基神经酰胺盒式方法有效合成Lacto-Ganglio系列神经节苷脂：神经节苷脂X2的总合成
4. The First Total Synthesis of Ganglioside HPG-7 [C] . Iwavama Y., Ando H., Ishida H. International Carbohydrate Symposium . 2013

机译：神经节苷脂HPG-7的第一个合成
5. Part I: The first regio- and atropdiastereoselective total synthesis of the dimeric indole alkaloid (+)-dispegatrine, as well as the first total synthesis of the sarpagine alkaloids (+)-spegatrine, lochvinerine, (+)-lochneram and an improved total synthesis of (+)-10-methoxyvellosimine, (+)-lochnerine and (+)-sarpagine. Part II: Studies directed toward the total synthesis of the carbon-19 methyl substituted sarpagine-macroline alkaloids (+)-macro-salhine chloride as well as macrocarpine A, B and C. [D] . Edwankar, Chitra R. 2011

机译：第一部分：二聚吲哚生物碱（+）-dispegatrine的第一个区域和对映异构选择性全合成，以及sarpagine生物碱（+）-spegatrine，lochvinerine，（+）-lochneram的第一个全合成（+）-10-甲氧基玻璃素胺，（+）-氯精胺和（+）-sarpagine的合成。第二部分：研究碳19甲基取代的沙雷帕金-大麦碱生物碱（+）-大-沙丁鱼碱氯化物以及大芸香碱A，B和C的总合成。
6. Extending the Glucosyl Ceramide Cassette Approach: Application in the Total Synthesis of Ganglioside GalNAc-GM1b [O] . Miku Konishi, Akihiro Imamura, Kohki Fujikawa, 2013

机译：扩展葡萄糖基神经酰胺盒法：在神经节苷脂GalNAc-GM1b的全合成中的应用
7. Extending the Glucosyl Ceramide Cassette Approach: Application in the Total Synthesis of Ganglioside GalNAc-GM1b [O] . Miku Konishi, Akihiro Imamura, Kohki Fujikawa, 2013

机译：扩展葡萄糖神经酰胺盒式方法：在神经节苷脂GalNac-Gm1b全合成中的应用

A First Total Synthesis of Ganglioside HLG-2

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