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Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.
Org Biomol Chem. 2014 Jul 21; 12(27):4816-9.OB

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.

Authors+Show Affiliations

Centre for Analysis and Synthesis, Department of Chemistry, Lund University, POB 124, SE-22100, Lund, Sweden. ulf.nilsson@chem.lu.se.No affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24867410

Citation

Mandal, S, and U J. Nilsson. "Tri-isopropylsilyl Thioglycosides as Masked Glycosyl Thiol Nucleophiles for the Synthesis of S-linked Glycosides and Glyco-conjugates." Organic & Biomolecular Chemistry, vol. 12, no. 27, 2014, pp. 4816-9.
Mandal S, Nilsson UJ. Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates. Org Biomol Chem. 2014;12(27):4816-9.
Mandal, S., & Nilsson, U. J. (2014). Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates. Organic & Biomolecular Chemistry, 12(27), 4816-9. https://doi.org/10.1039/c4ob00741g
Mandal S, Nilsson UJ. Tri-isopropylsilyl Thioglycosides as Masked Glycosyl Thiol Nucleophiles for the Synthesis of S-linked Glycosides and Glyco-conjugates. Org Biomol Chem. 2014 Jul 21;12(27):4816-9. PubMed PMID: 24867410.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates. AU - Mandal,S, AU - Nilsson,U J, PY - 2014/5/29/entrez PY - 2014/5/29/pubmed PY - 2015/6/6/medline SP - 4816 EP - 9 JF - Organic & biomolecular chemistry JO - Org. Biomol. Chem. VL - 12 IS - 27 N2 - 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. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/24867410/Tri_isopropylsilyl_thioglycosides_as_masked_glycosyl_thiol_nucleophiles_for_the_synthesis_of_S_linked_glycosides_and_glyco_conjugates_ L2 - https://doi.org/10.1039/c4ob00741g DB - PRIME DP - Unbound Medicine ER -