30319-44-9Relevant articles and documents
Synthesis of a Tridecasaccharide Lipooligosaccharide Antigen from the Opportunistic Pathogen Mycobacterium kansasii
Bai, Bing,Liu, Yu-Hsuan,Lowary, Todd L.,Shen, Ke
supporting information, p. 24859 - 24863 (2021/10/25)
The outer surfaces of mycobacteria, including the organism that causes tuberculosis, are decorated with an array of immunomodulatory glycans. Among these are lipooligosaccharides (LOSs), a class of molecules for which the function remains poorly understoo
Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities
Sampei, Mana,Arai, Midori A.,Ishibashi, Masami
, p. 651 - 654 (2018/04/16)
Lignans are widely distributed in plants and exhibit significant pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca b
Stereoselective Epimerizations of Glycosyl Thiols
Doyle, Lisa M.,O'Sullivan, Shane,Di Salvo, Claudia,McKinney, Michelle,McArdle, Patrick,Murphy, Paul V.
supporting information, p. 5802 - 5805 (2017/11/10)
Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.