Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens

Sanyong Zhu; Ganesh Samala; Eric T. Sletten; Jennifer L. Stockdill; Hien M. Nguyen

doi:10.1039/c9sc04079j

Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens

Chemical Science ◽

10.1039/c9sc04079j ◽

2019 ◽

Vol 10 (45) ◽

pp. 10475-10480 ◽

Cited By ~ 5

Author(s):

Sanyong Zhu ◽

Ganesh Samala ◽

Eric T. Sletten ◽

Jennifer L. Stockdill ◽

Hien M. Nguyen

Keyword(s):

Chemical Stability ◽

Triflic Acid ◽

Acid Catalyzed

Studies of S-linked glycoconjugates have attracted growing interest because of their enhanced chemical stability and enzymatic resistance over O-glycoside counterparts.

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ChemInform Abstract: Synthetic Methods and Reactions. Part 158. Trifluoromethanesulfonic ( Triflic) Acid-Catalyzed Transformations of α-Hydroxy Carbonyl Compounds.

ChemInform ◽

10.1002/chin.199134144 ◽

2010 ◽

Vol 22 (34) ◽

pp. no-no

Author(s):

G. A. OLAH ◽

A. WU

Keyword(s):

Carbonyl Compounds ◽

Synthetic Methods ◽

Triflic Acid ◽

Acid Catalyzed

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Triflic Acid Catalyzed Additions of 2-Alkoxycarbonyl Allylboronates to Aldehydes. Study of Scope and Mechanistic Investigation of the Reaction Stereochemistry.

ChemInform ◽

10.1002/chin.200727088 ◽

2007 ◽

Vol 38 (27) ◽

Author(s):

Tim G. Elford ◽

Yuichiro Arimura ◽

Siu Hong Yu ◽

Dennis G. Hall

Keyword(s):

Triflic Acid ◽

Mechanistic Investigation ◽

Acid Catalyzed

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Triflic Acid-Catalyzed Synthesis of Indole-Substituted Indane Derivatives via In Situ Formed Acetal-Facilitated Nucleophilic Addition and 4π-Electron-5-Carbon Electrocyclization Sequence

The Journal of Organic Chemistry ◽

10.1021/acs.joc.1c01396 ◽

2021 ◽

Author(s):

Golla Ramesh ◽

Rengarajan Balamurugan

Keyword(s):

Nucleophilic Addition ◽

Triflic Acid ◽

Acid Catalyzed

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Triflic Acid Catalyzed Synthesis of Spirocycles via Acetylene Cations

Angewandte Chemie International Edition ◽

10.1002/anie.200901771 ◽

2009 ◽

Vol 48 (32) ◽

pp. 5893-5896 ◽

Cited By ~ 65

Author(s):

Tienan Jin ◽

Masafumi Himuro ◽

Yoshinori Yamamoto

Keyword(s):

Triflic Acid ◽

Acid Catalyzed

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Triflic acid-catalyzed cascade cyclization of arenyl enynes via acetylene-cation cyclization and Friedel–Crafts type reaction

Tetrahedron Letters ◽

10.1016/j.tetlet.2010.10.094 ◽

2011 ◽

Vol 52 (17) ◽

pp. 2069-2071 ◽

Cited By ~ 27

Author(s):

Tienan Jin ◽

Junichi Uchiyama ◽

Masafumi Himuro ◽

Yoshinori Yamamoto

Keyword(s):

Triflic Acid ◽

Type Reaction ◽

Cascade Cyclization ◽

Acid Catalyzed

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ChemInform Abstract: The Triflic Acid-Catalyzed Deacylation and Decarboxylation of Polymethylbenzenecarbonyl Derivatives Under Mild Conditions.

ChemInform ◽

10.1002/chin.198924113 ◽

1989 ◽

Vol 20 (24) ◽

Author(s):

T. KEUMI ◽

T. MORITA ◽

Y. OZAWA ◽

H. KITAJIMA

Keyword(s):

Triflic Acid ◽

Mild Conditions ◽

Acid Catalyzed

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Triflic Acid Catalyzed 1,6-Conjugate Addition of Thiols to p -Quinone Methides under Continuous-Flow Conditions

European Journal of Organic Chemistry ◽

10.1002/ejoc.201700587 ◽

2017 ◽

Vol 2017 (25) ◽

pp. 3716-3721 ◽

Cited By ~ 17

Author(s):

Abhijeet S. Jadhav ◽

Ramasamy Vijaya Anand

Keyword(s):

Continuous Flow ◽

Conjugate Addition ◽

Flow Conditions ◽

Triflic Acid ◽

Quinone Methides ◽

Acid Catalyzed

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Synthetic methods and reactions. 188. Triflic acid catalyzed phenylamination of aromatics with phenyl azide

The Journal of Organic Chemistry ◽

10.1021/jo00076a063 ◽

1993 ◽

Vol 58 (24) ◽

pp. 6900-6901 ◽

Cited By ~ 15

Author(s):

George A. Olah ◽

Pichika Ramaiah ◽

Qi Wang ◽

G. K. Surya Prakash

Keyword(s):

Synthetic Methods ◽

Triflic Acid ◽

Phenyl Azide ◽

Acid Catalyzed

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Synthesis of tertiary amines by direct Brønsted acid catalyzed reductive amination

Chemical Communications ◽

10.1039/d0cc02955f ◽

2020 ◽

Vol 56 (61) ◽

pp. 8691-8694

Author(s):

Mohanad A. Hussein ◽

An H. Dinh ◽

Vien T. Huynh ◽

Thanh Vinh Nguyen

Keyword(s):

Carbonyl Compounds ◽

Reductive Amination ◽

Bronsted Acid ◽

Tertiary Amines ◽

Brønsted Acid ◽

Triflic Acid ◽

Brönsted Acid ◽

Acid Catalyzed

Triflic acid efficiently promotes the reductive amination reactions of carbonyl compounds on a broad range of substrates.

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ChemInform Abstract: Triflic Acid-Catalyzed Enynes Cyclization: A New Strategy Beyond Electrophilic π-Activation.

ChemInform ◽

10.1002/chin.201644033 ◽

2016 ◽

Vol 47 (44) ◽

Author(s):

Zhunzhun Yu ◽

Lu Liu ◽

Junliang Zhang

Keyword(s):

Triflic Acid ◽

New Strategy ◽

Acid Catalyzed

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