Literature DB >> 15876041

Preparation of 1-thio uronic acid lactones and their use in oligosaccharide synthesis.

Leendert J van den Bos1, Remy E J N Litjens, Richard J B H N van den Berg, Herman S Overkleeft, Gijsbert A van der Marel.   

Abstract

The chemo- and regioselective TEMPO/BAIB-mediated oxidation of 2,6- and 3,6-dihydroxy 1-thio glycopyranosides to the corresponding 1-thio uronic acid lactones is described. These locked 1-thio glycuronides can directly be used as donors in glycosidation reactions using the Ph(2)SO/Tf(2)O reagent system. Alternatively, selective opening of the lactone bridge liberates a hydroxyl function for ensuing glycosylations.

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Year:  2005        PMID: 15876041     DOI: 10.1021/ol050491y

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  A facile method for oxidation of primary alcohols to carboxylic acids and its application in glycosaminoglycan syntheses.

Authors:  Lijun Huang; Nardos Teumelsan; Xuefei Huang
Journal:  Chemistry       Date:  2006-07-05       Impact factor: 5.236

2.  Design and syntheses of hyaluronan oligosaccharide conjugates as inhibitors of CD44-Hyaluronan binding.

Authors:  Xiaowei Lu; Xuefei Huang
Journal:  Glycoconj J       Date:  2015-05-22       Impact factor: 2.916

3.  Hydrogen bond activated glycosylation under mild conditions.

Authors:  Ke Xiao; Yongxin Hu; Yongyong Wan; XinXin Li; Qin Nie; Hao Yan; Liming Wang; Jinxi Liao; Deyong Liu; Yuanhong Tu; Jiansong Sun; Jeroen D C Codée; Qingju Zhang
Journal:  Chem Sci       Date:  2021-12-15       Impact factor: 9.825

  3 in total

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