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New Diacylamino Protecting Groups for Glucosamine
Author(s) -
Aly Mohamed R. E.,
Schmidt Richard R.
Publication year - 2005
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.200500107
Subject(s) - chemistry , disaccharide , glycosyl , glucosamine , yield (engineering) , cleavage (geology) , glycosyl donor , derivative (finance) , stereochemistry , glycoside , catalysis , protecting group , acceptor , glycosylation , medicinal chemistry , organic chemistry , biochemistry , materials science , alkyl , geotechnical engineering , physics , fracture (geology) , economics , financial economics , engineering , metallurgy , condensed matter physics
Glucosamine was transformed into N ‐diphenylmaleoyl (DPM), N ‐(3,3‐dimethylglutaryl) (DMG), and N ‐diglycolyl (DG) derivatives which furnished O ‐acetyl‐protected O ‐glycosyl trichloroacetimidates 3 , 12 , and 20 , respectively, as glycosyl donors. Their reactions with various acceptors 4 in the presence of TMSOTf as catalyst afforded the corresponding β‐glycosides 5a – c , 13a – e , and 21a , d , f , g generally in high yields. Investigations into the cleavage of the N ‐protecting groups led to good results for the DPM and DG groups. 3‐ O ‐Unprotected glucosamine derivative 24 with N ‐DG protection also served well as an acceptor, as shown in its reaction with galactosyl donor 25 which led to disaccharide 26 in very high yield. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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