A New and Efficient Approach to Prepare N-Acetyl GM3 Ganglioside via Trisaccharide [1鈫?] Lactone

详细信息    查看全文

• 作者：Abel Regalado Calder铆n ; Miriam Mesa Hern谩ndez ; Diamela Ch谩vez Pi帽eiro ; Ricelia Gonz谩lez Serpa ; L谩zaro Andr茅s Monteser铆n Castanedo ; Mar铆a del Carmen Rodr铆guez Montero ; Blanca Tol贸n Murg铆a ; Roberto Carlos Veloso Pita ; Raine Garrido Arteaga ; Violeta Fern谩ndez Santana ; Vicente Verez Bencomo ; Miguel Antonio L贸pez L贸pez
• 刊名：Organic Process Research & Development
• 出版年：2013
• 出版时间：January 18, 2013
• 年：2013
• 卷：17
• 期：1
• 页码：53-60
• 全文大小：270K
• 年卷期：v.17,no.1(January 18, 2013)
• ISSN：1520-586X

文摘

The N-acetyl GM₃ ganglioside (NAcGM₃) is an important glycosphingolipid currently used to prepare a new therapeutic cancer vaccine. Some quantities of this ganglioside were obtained by using [1鈫?] lactone as the trisaccharide protective function. Thus, sialylation of hexabenzyllactose acceptor with 5-acetyl neuraminylthiophenyl donor afforded the (2鈫?) trisaccharide as an 伪/尾 (3:1) mixture. The 伪-anomer was isolated through selective [1鈫?] lactone formation followed by chromatography. The lactone was hydrogenolyzed, per-O-acetylated, and selectively deacetylated, and a trichloroacetimidate donor was synthesized from the obtained compound. Azidosphingosine glycosylation, followed by azide group reduction and acylation of the resulting amino glycoside with stearic acid provided the protected ganglioside, which was finally subjected to the Zemplen鈥檚 procedure, before saponification, to obtain the NAcGM₃ in an overall yield of 11.5% at multigram scale.