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Literature DB >> 24867410

Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.

Abstract

Tri-isopropylsilyl thio-glycosides (TIPS S-glycosides) were synthesized through base promoted SN2 substitution of glycosyl halides with TIPS-SH or by Lewis acid promoted glycosylation of TIPS-SH with glycosyl acetates or p-methoxyphenyl glycosides. Various thioglycoside derivatives were obtained in high yields by one-pot fluoride-mediated de-silylation and thiol alkylation with alkyl halides or Michael acceptors of one common TIPS S-glycoside.

Entities: Chemical Gene

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Year: 2014 PMID： 24867410 DOI： 10.1039/c4ob00741g

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

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Cited

3 in total

1. Hybrid ligands with calixarene and thiodigalactoside groups: galectin binding and cytotoxicity.

Authors: Hao Zhang; Hans Ippel; Michelle C Miller; Tse J Wong; Arjan W Griffioen; Kevin H Mayo; Roland J Pieters
Journal: Org Chem Front Date: 2019-07-12 Impact factor: 5.281

2. Thiodigalactoside-Bovine Serum Albumin Conjugates as High-Potency Inhibitors of Galectin-3: An Outstanding Example of Multivalent Presentation of Small Molecule Inhibitors.

Authors: Hao Zhang; Dominic Laaf; Lothar Elling; Roland J Pieters
Journal: Bioconjug Chem Date: 2018-03-07 Impact factor: 4.774

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

Authors: Sanyong Zhu; Ganesh Samala; Eric T Sletten; Jennifer L Stockdill; Hien M Nguyen
Journal: Chem Sci Date: 2019-10-01 Impact factor: 9.825

3 in total

Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.

1. Hybrid ligands with calixarene and thiodigalactoside groups: galectin binding and cytotoxicity.

2. Thiodigalactoside-Bovine Serum Albumin Conjugates as High-Potency Inhibitors of Galectin-3: An Outstanding Example of Multivalent Presentation of Small Molecule Inhibitors.

3. 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.

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