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

A convenient and efficient approach was developed to synthesize α-Kdo -glycosides based on the Tf O/( -Tol) SO preactivation strategy using peracetylated Kdo thioglycoside as a donor. Under the optimized reaction conditions, several -glycoside products, including α-(2 → 1)-, α-(2 → 2)-, α-(2 → 3)-,...

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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 United States 09.06.2023
Subjects
Cardiac Glycosides
Glycosides
Glycosylation
Lipopolysaccharides
Sugar Acids
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Abstract A convenient and efficient approach was developed to synthesize α-Kdo -glycosides based on the Tf O/( -Tol) SO preactivation strategy using peracetylated Kdo thioglycoside as a donor. Under the optimized reaction conditions, several -glycoside products, including α-(2 → 1)-, α-(2 → 2)-, α-(2 → 3)-, and α-(2 → 6)-Kdo products, were stereoselectively synthesized in high yields. Remarkably, a series of aromatic α-Kdo -glycosides were first and successfully constructed in high yields. An S 2-like mechanism was revealed by DFT calculations and experimental results.
AbstractList A convenient and efficient approach was developed to synthesize α-Kdo -glycosides based on the Tf O/( -Tol) SO preactivation strategy using peracetylated Kdo thioglycoside as a donor. Under the optimized reaction conditions, several -glycoside products, including α-(2 → 1)-, α-(2 → 2)-, α-(2 → 3)-, and α-(2 → 6)-Kdo products, were stereoselectively synthesized in high yields. Remarkably, a series of aromatic α-Kdo -glycosides were first and successfully constructed in high yields. An S 2-like mechanism was revealed by DFT calculations and experimental results.
Author Liu, Si-Cong
Liu, Yi-Jiang
Xing, Guo-Wen
Geng, Zhu-Feng
Chang, Le
Liu, Guang-Jian
Ma, Qing-Yu
Gao, Xiao-Jie
Fang, De-Cai
Zhang, Jing-Dong
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CitedBy_id crossref_primary_10_1016_j_gresc_2024_03_004
crossref_primary_10_1002_ange_202313985
crossref_primary_10_1002_anie_202313985
crossref_primary_10_1039_D4OB00182F
crossref_primary_10_1016_j_cclet_2024_109972
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Snippet A convenient and efficient approach was developed to synthesize α-Kdo -glycosides based on the Tf O/( -Tol) SO preactivation strategy using peracetylated Kdo...
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SubjectTerms Cardiac Glycosides
Glycosides
Glycosylation
Lipopolysaccharides
Sugar Acids
Title α-Stereoselective 3-Deoxy-d- manno -oct-2-ulosonoic Acid (Kdo) O -Glycosylation with a p -Toluenethioglycoside Donor by the ( p -Tol) 2 SO/Tf 2 O Preactivation Strategy
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