Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media

Anup Kumar Misra, Éva Bokor, Sándor Kun, Evelin Bolyog-Nagy, A. Kathó, Ferenc Joó, L. Somsák

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

[RuCl2(DMSO)4] in the presence of N-benzylated 1,3,5-triaza-7-phosphaadamantane efficiently catalyzed the hydration of glycosyl cyanides to the corresponding formamide derivatives in water or water-N-methylpyrrolidone solvent mixtures at 105 °C. O-Acetyl, O-benzoyl, and O-benzyl protecting groups, anomeric bromide and azide substituents as well as double bonds were shown to be compatible with these reaction conditions.

Original languageEnglish
Pages (from-to)5995-5998
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number44
DOIs
Publication statusPublished - Oct 28 2015

Fingerprint

Formamides
Ruthenium
Cyanides
Hydration
Azides
Water
Bromides
Derivatives

Keywords

  • Amide
  • C-Glycoside
  • Nitrile
  • Ruthenium complex
  • Water

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media. / Misra, Anup Kumar; Bokor, Éva; Kun, Sándor; Bolyog-Nagy, Evelin; Kathó, A.; Joó, Ferenc; Somsák, L.

In: Tetrahedron Letters, Vol. 56, No. 44, 28.10.2015, p. 5995-5998.

Research output: Contribution to journalArticle

Misra, Anup Kumar ; Bokor, Éva ; Kun, Sándor ; Bolyog-Nagy, Evelin ; Kathó, A. ; Joó, Ferenc ; Somsák, L. / Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 44. pp. 5995-5998.
@article{16110c4f8afc4103b91018907ab5ffb9,
title = "Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media",
abstract = "[RuCl2(DMSO)4] in the presence of N-benzylated 1,3,5-triaza-7-phosphaadamantane efficiently catalyzed the hydration of glycosyl cyanides to the corresponding formamide derivatives in water or water-N-methylpyrrolidone solvent mixtures at 105 °C. O-Acetyl, O-benzoyl, and O-benzyl protecting groups, anomeric bromide and azide substituents as well as double bonds were shown to be compatible with these reaction conditions.",
keywords = "Amide, C-Glycoside, Nitrile, Ruthenium complex, Water",
author = "Misra, {Anup Kumar} and {\'E}va Bokor and S{\'a}ndor Kun and Evelin Bolyog-Nagy and A. Kath{\'o} and Ferenc Jo{\'o} and L. Soms{\'a}k",
year = "2015",
month = "10",
day = "28",
doi = "10.1016/j.tetlet.2015.09.040",
language = "English",
volume = "56",
pages = "5995--5998",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "44",

}

TY - JOUR

T1 - Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media

AU - Misra, Anup Kumar

AU - Bokor, Éva

AU - Kun, Sándor

AU - Bolyog-Nagy, Evelin

AU - Kathó, A.

AU - Joó, Ferenc

AU - Somsák, L.

PY - 2015/10/28

Y1 - 2015/10/28

N2 - [RuCl2(DMSO)4] in the presence of N-benzylated 1,3,5-triaza-7-phosphaadamantane efficiently catalyzed the hydration of glycosyl cyanides to the corresponding formamide derivatives in water or water-N-methylpyrrolidone solvent mixtures at 105 °C. O-Acetyl, O-benzoyl, and O-benzyl protecting groups, anomeric bromide and azide substituents as well as double bonds were shown to be compatible with these reaction conditions.

AB - [RuCl2(DMSO)4] in the presence of N-benzylated 1,3,5-triaza-7-phosphaadamantane efficiently catalyzed the hydration of glycosyl cyanides to the corresponding formamide derivatives in water or water-N-methylpyrrolidone solvent mixtures at 105 °C. O-Acetyl, O-benzoyl, and O-benzyl protecting groups, anomeric bromide and azide substituents as well as double bonds were shown to be compatible with these reaction conditions.

KW - Amide

KW - C-Glycoside

KW - Nitrile

KW - Ruthenium complex

KW - Water

UR - http://www.scopus.com/inward/record.url?scp=84944227254&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84944227254&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.09.040

DO - 10.1016/j.tetlet.2015.09.040

M3 - Article

VL - 56

SP - 5995

EP - 5998

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 44

ER -