alpha-Stereoselective 3-Deoxy-d-manno-oct-2-ulosonoic Acid (Kdo) O-Glycosylation with a p-Toluenethioglycoside Donor by the (p-Tol)(2)SO/Tf2O Preactivation Strategy

A convenient and efficient approach was developed tosynthesize alpha-Kdo O-glycosides based on the Tf2O/(p-Tol)(2)SO preactivation strategy usingperacetylated Kdo thioglycoside as a donor. Under the optimized reactionconditions, several O-glycoside products, including alpha-(2 -> 1)-, alpha-(2 -&...

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Published inOrganic letters Vol. 25; no. 22; pp. 4150 - 4155
Main Authors Zhang, Jing-dong, Gao, Xiao-jie, Liu, Si-cong, Geng, Zhu-feng, Chang, Le, Liu, Yi-jiang, Ma, Qing-yu, Xing, Guo-wen, Liu, Guang-jian, Fang, De-cai
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 30.05.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TETRASACCHARIDE
LIPOPOLYSACCHARIDE
CHEMISTRY
ION
INNER-CORE
DERIVATIVES
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Summary:A convenient and efficient approach was developed tosynthesize alpha-Kdo O-glycosides based on the Tf2O/(p-Tol)(2)SO preactivation strategy usingperacetylated Kdo thioglycoside as a donor. Under the optimized reactionconditions, several O-glycoside products, including alpha-(2 -> 1)-, alpha-(2 -> 2)-, alpha-(2 -> 3)-, and alpha-(2 -> 6)-Kdo products, were stereoselectivelysynthesized in high yields. Remarkably, a series of aromatic alpha-Kdo O-glycosides were first and successfully constructed inhigh yields. An S(N)2-like mechanism was revealed by DFTcalculations and experimental results.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01430