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Synthesis of Glycosylamines from Glycosyl Isothiocyanates and Bis(tributyltin) Oxide
Author(s) -
IsacGarcía Joaquin,
CalvoFlores Francisco G.,
HernándezMateo Fernando,
SantoyoGonzález Francisco
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200101)2001:2<383::aid-ejoc383>3.0.co;2-n
Subject(s) - chemistry , glycosyl , tributyltin , organic chemistry
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.