1023290-63-2Relevant academic research and scientific papers
Synthesis and characterization of sulfated gal-β-1,3/4-GlcNAc disaccharides through consecutive protection/glycosylation steps
Tu, Zhijay,Hsieh, Hsiao-Wu,Tsai, Chih-Ming,Hsu, Chia-Wei,Wang, Shy-Guey,Wu, Kuan-Jung,Lin, Kuo-I,Lin, Chun-Hung
supporting information, p. 1536 - 1550 (2013/07/26)
We have developed an expeditious procedure to yield large amounts of orthogonally protected Gal-β1,3/4-GlcNAc, which allowed for the systematic introduction of a sulfate group onto the C3/C6 positions of Gal and/or the C6 position of GlcNAc. In particular
Chemical synthesis of a hyaluronic acid decasaccharide
Lu, Xiaowei,Kamat, Medha N.,Huang, Lijun,Huang, Xuefei
experimental part, p. 7608 - 7617 (2010/03/01)
(Chemical Equation Presented) The chemical synthesis of a hyaluronic acid decasaccharide using the preactivation-based chemoselective glycosylation strategy is described. Assembly of large oligosaccharides is generally challenging due to the increased difficulties in both glycosylation and deprotection. Indeed, the same building blocks previously employed for hyaluronic acid hexasaccharide syntheses failed to yield the desired decasaccharide. After extensive experimentation, the decasaccharide backbone was successfully constructed with an overall yield of 37% from disaccharide building blocks. The trichloroacetyl group was used as the nitrogen protective group for the glucosamine units, and the addition of TMSOTf was found to be crucial to suppress the formation of trichloromethyl oxazoline side product and enable high glycosylation yield. For deprotections, the combination of a mild basic condition and the monitoring methodology using 1H NMR allowed the removal of all base-labile protective groups, which facilitated the generation of the fully deprotected HA decasaccharide.
Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides
Chao, Chin-Sheng,Chen, Min-Chun,Lin, Shih-Che,Mong, Kwok-Kong T.
, p. 957 - 964 (2008/09/17)
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.
