Gram-scale syntheses of the (1 → 3)-linked and (1 → 4)-linked hyaluronan disaccharides
Gram-scale syntheses of the (1 → 3)-linked and (1 → 4)-linked hyaluronan disaccharides
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DOI:
10.1016/j.carres.2004.03.005
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发表时间:
2004-05-17
影响因子:
3.1
通讯作者:
Petillo, PA
中科院分区:
文献类型:
--
作者:
Adamski-Werner, SL;Yeung, BKS;Petillo, PA
The first gram-scale syntheses of two hyaluronan disaccharides are described. Construction of the (1 --> 4)-linked disaccharide 12 was achieved in 12% overall yield using 2,3-bis-dimethyl acetal protection in combination with chlorosilane-induced carbamate cleavage methodologies. The uronic acid functionality was installed using TEMPO oxidation with NaOCl as the hypochlorite source. The (1 --> 3)-linked disaccharide 18 was achieved in 7% overall yield utilizing acetonide protection in addition to the chlorosilane-induced carbamate cleavage methodology and the TEMPO oxidation. (C) 2004 Elsevier Ltd. All rights reserved.