Synthesis of glycosylthiols and reactivity studies

Dere, Ravindra T.; Kumar, Amit; Kumar, Vipin; Zhu, Xiangming; Schmidt, Richard R.

Synthesis of glycosylthiols and reactivity studies

Dateien

Schmidt etal.pdf(972.76 KB)

Datum

2011

Autor:innen

Dere, Ravindra T.

Kumar, Amit

Kumar, Vipin

Zhu, Xiangming

Schmidt, Richard R.

Publikationstyp

Zeitschriftenartikel

Erschienen in

The Journal of Organic Chemistry ; 76 (2011), 18. - S. 7539-7545. - ISSN 0022-3263. - eISSN 1520-6904

Zusammenfassung

The acid-catalyzed reaction of 1,2-anhydro-3,4,6-tri-Obenzyl- R-D-glucopyranose (7) as glycosyl donor with bis-trimethylsilyl sulfide as acceptor affords the R-thiol. Hence, this sterically hindered S-nucleophile as acceptor should provide with O-glycosyl trichloroacetimidates as glycosyl donors that have nonparticipating groups at C-2, glycosylthiols with the thiol group in axial position. This was confirmed for various donors (4, 16-19) with the exception of the corresponding mannosyl donor (20). However, powerful participating groups at C-2 of the donor (23-28) governed the anomeric selectivity.

Fachgebiet (DDC)

540 Chemie

Zitieren

ISO 690

DERE, Ravindra T., Amit KUMAR, Vipin KUMAR, Xiangming ZHU, Richard R. SCHMIDT, 2011. Synthesis of glycosylthiols and reactivity studies. In: The Journal of Organic Chemistry. 76(18), pp. 7539-7545. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/jo200624e

BibTex

@article{Dere2011-09-16Synth-18128,
  year={2011},
  doi={10.1021/jo200624e},
  title={Synthesis of glycosylthiols and reactivity studies},
  number={18},
  volume={76},
  issn={0022-3263},
  journal={The Journal of Organic Chemistry},
  pages={7539--7545},
  author={Dere, Ravindra T. and Kumar, Amit and Kumar, Vipin and Zhu, Xiangming and Schmidt, Richard R.}
}

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