Premium
Simple and Rapid Procedures for the Synthesis of 5‐Acylated 4β‐Acylamido‐ and 4β‐Acetoxyneuraminic Acid Glycals
Author(s) -
Agnolin Irene S.,
Rota Paola,
Allevi Pietro,
Gregorio Antonio,
Anastasia Mario
Publication year - 2012
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/ejoc.201201001
Subject(s) - chemistry , glycal , oxazoline , organic chemistry , derivative (finance) , combinatorial chemistry , acylation , stereochemistry , catalysis , stereoselectivity , financial economics , economics
Two simple and rapid procedures affording 4β‐acylamido‐ and 4β‐acetoxyneuraminic acid glycals acylated or perfluoroacylated at the 5‐amino group are reported. The first protocol avoids the formation of oxazolines to synthesize the 4β‐acetamido glycals through the Ritter reaction. The second passes through the oxazoline derivative to prepare 4β‐acetoxyneuraminic acid glycals. Both protocols start from peracetylated methyl neuraminate, acylated at the amino group with a normal, a glycolyl, or a perfluoroacyl group, or with the corresponding peracetylated glycal methyl esters (of the DANA or FANA series).