Browsing by Author "Lin, Shih-Che"

Now showing 1 - 2 of 2

Joined use of oxazolidinone and desymmetric amino protection: a new strategy for protection of glucosamine
(2010-04-07)
Lin, Shih-Che
;
Chao, Chin-Sheng
;
Chang, Chiu-Ching
;
Mong, Kwok-Kong T.
;
應用化學系
Joined use of N-benzyl oxazolidinone and N-benzyl-N-benzyloxycarbonyl (N-BnCbz) desymmetric amino-protecting function is reported. The new synthetic approach enables the facile preparation of type I and type 2 LacNAc disaccharides in satisfactory yields. One-pot deprotection of N-BnCbz and O-benzyl ether is achieved by hydrogenolysis under mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.
Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides
(2008-04-07)
Chao, Chin-Sheng
;
Chen, Min-Chun
;
Lin, Shih-Che
;
Mong, Kwok-Kong T.
;
應用化學系
Inexpensive and readily available sulfonic acids, p-toluenesulfonic acid, and sulfuric acid are versatile and efficient catalysts for the peracetylation of a broad spectrum of carbohydrate substrates in good yield and in a practical time frame. Three appealing features in sulfonic acid-catalyzed acetylation of free sugars were explored including (1) suppression of furanosyl acetate formation for D-galactose and L-fucose; (2) high yielding chemoselective acetylation of sialic acid under appropriate conditions; and (3) peracetylation of amino sugars with different amino protecting functions. Simple one-pot two step acetylation-thioglycosidation methods for the expeditious synthesis of p-tolyl per-O-acetyl thioglycosides were also delineated. (C) 2008 Elsevier Ltd. All rights reserved.