Synthesis of Glycosylamines from Glycosyl Isothiocyanates and Bis(tributyltin) Oxide
2001; Wiley; Volume: 2001; Issue: 2 Linguagem: Inglês
10.1002/1099-0690(200101)2001
ISSN1434-193X
AutoresJoaquín Isac‐García, Francisco G. Calvo‐Flores, Fernando Hernández-Matéo, Francisco Santoyo‐González,
Tópico(s)Chemical Synthesis and Analysis
ResumoEuropean Journal of Organic ChemistryVolume 2001, Issue 2 p. 383-390 Full Paper Synthesis of Glycosylamines from Glycosyl Isothiocyanates and Bis(tributyltin) Oxide Joaquin Isac-García, Joaquin Isac-García Instituto de Biotecnología, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Campus Fuentenueva s/n, 18071 Granada, Spain, Fax: (internat.) +34-95/824-3187Search for more papers by this authorFrancisco G. Calvo-Flores, Francisco G. Calvo-Flores Instituto de Biotecnología, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Campus Fuentenueva s/n, 18071 Granada, Spain, Fax: (internat.) +34-95/824-3187Search for more papers by this authorFernando Hernández-Mateo, Fernando Hernández-Mateo Instituto de Biotecnología, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Campus Fuentenueva s/n, 18071 Granada, Spain, Fax: (internat.) +34-95/824-3187Search for more papers by this authorFrancisco Santoyo-González, Francisco Santoyo-González [email protected] Instituto de Biotecnología, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Campus Fuentenueva s/n, 18071 Granada, Spain, Fax: (internat.) +34-95/824-3187Search for more papers by this author Joaquin Isac-García, Joaquin Isac-García Instituto de Biotecnología, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Campus Fuentenueva s/n, 18071 Granada, Spain, Fax: (internat.) +34-95/824-3187Search for more papers by this authorFrancisco G. Calvo-Flores, Francisco G. Calvo-Flores Instituto de Biotecnología, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Campus Fuentenueva s/n, 18071 Granada, Spain, Fax: (internat.) +34-95/824-3187Search for more papers by this authorFernando Hernández-Mateo, Fernando Hernández-Mateo Instituto de Biotecnología, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Campus Fuentenueva s/n, 18071 Granada, Spain, Fax: (internat.) +34-95/824-3187Search for more papers by this authorFrancisco Santoyo-González, Francisco Santoyo-González [email protected] Instituto de Biotecnología, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Campus Fuentenueva s/n, 18071 Granada, Spain, Fax: (internat.) +34-95/824-3187Search for more papers by this author First published: 21 December 2000 https://doi.org/10.1002/1099-0690(200101)2001:2 3.0.CO;2-NCitations: 15Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract The synthesis of glycopyranosylamines is described from the reaction of glycopyranosyl isothiocynates with bis(tributyltin) oxide. The method is simple and efficient allowing, under very mild conditions, the synthesis of N-acyl glycopyranosylamines in one pot. The reactions were performed using both 2-deoxy-2-iodo glycopyranosyl isothiocyanates and glycopyranosyl isothiocyanates derived from mono- and disaccharides. Anomerization was observed when the starting materials were α-glycopyranosyl derivatives. The methodology has also been applied for the preparation of several glycosyl amino acids. References 1 H. Lis , N. Sharon , Eur. J. Biochem. 1993 , 218 , 1 −27 . 10.1111/j.1432-1033.1993.tb18347.x CASPubMedWeb of Science®Google Scholar 2 A. Varki , Glycobiology 1993 , 3 , 97 −130 . 10.1093/glycob/3.2.97 CASPubMedWeb of Science®Google Scholar 3 H. Garg , R. W. Jeanloz , Adv. Carbohydr. Chem. 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