KOPS - Das Institutionelle Repositorium der Universität Konstanz

Preparation and transmetallation of a triphenylstannyl beta-D-glucopyranoside : a highly stereoselective route to beta-D-C-Glycosides via glycosyl dianions

Preparation and transmetallation of a triphenylstannyl beta-D-glucopyranoside : a highly stereoselective route to beta-D-C-Glycosides via glycosyl dianions

Zitieren

Dateien zu dieser Ressource

Prüfsumme: MD5:a53c413525833cc34adeda137581a77d

FREY, Oliver, Matthias HOFFMANN, Valentin WITTMANN, Horst KESSLER, Peter UHLMANN, Andrea VASELLA, 1994. Preparation and transmetallation of a triphenylstannyl beta-D-glucopyranoside : a highly stereoselective route to beta-D-C-Glycosides via glycosyl dianions. In: Helvetica Chimica Acta. 77(7), pp. 2060-2069. ISSN 0018-019X. eISSN 1522-2675

@article{Frey1994Prepa-9646, title={Preparation and transmetallation of a triphenylstannyl beta-D-glucopyranoside : a highly stereoselective route to beta-D-C-Glycosides via glycosyl dianions}, year={1994}, doi={10.1002/hlca.19940770730}, number={7}, volume={77}, issn={0018-019X}, journal={Helvetica Chimica Acta}, pages={2060--2069}, author={Frey, Oliver and Hoffmann, Matthias and Wittmann, Valentin and Kessler, Horst and Uhlmann, Peter and Vasella, Andrea} }

Kessler, Horst Uhlmann, Peter Frey, Oliver Kessler, Horst First publ. in: Helvetica Chimica Acta 77 (1994), pp. 2060-2069 1994 Preparation and transmetallation of a triphenylstannyl beta-D-glucopyranoside : a highly stereoselective route to beta-D-C-Glycosides via glycosyl dianions The triphenylstannyl β-u-glucopyranoside 4 was synthesized in one step from the 1.2-anhydro-a-uglucopyranose 3 with (hiphenylstannyl)lithium (Scheme 1). Transmetallation of 4 with excess BuLi, followed by quenching the dianion 7 with CD,OD gave (1s)- 1,5-anhydro-3,4,6-tri-O-benzyl-1f -²H]-u-glucitol (8) in 81%<br />yield (Scheme 2). Trapping of 7 with benzaldehyde, isobutyraldehyde, or acroleine gave the expected β-Dconfigurated products 11,12, and 13 in good yields. Preparation of C-acyl glycosides from acid chlorides, such as acetyl or benzoyl chloride was not practicable, but addition of benzonitrile to 7 yielded 84% of the benzoylated product 14. Treatment of 7 with Me1 led to 15 (30%) along with 40% of 18, C-alkylation being accompanied by halogen-metal exchange. Prior addition of lithium 2-thienylcyanocuprate increased the yield of 15 to 50% and using dimethyl sulfate instead of Me1 led to 77% of 15. No α-D-anomers could be detected, except with ally1 bromide as the electrophile, which yielded in a 1:l mixture of the anomers 16 and 17. Hoffmann, Matthias Wittmann, Valentin Vasella, Andrea application/pdf Frey, Oliver Hoffmann, Matthias Vasella, Andrea 2011-03-24T18:13:25Z 2011-03-24T18:13:25Z Uhlmann, Peter Wittmann, Valentin eng deposit-license

Dateiabrufe seit 01.10.2014 (Informationen über die Zugriffsstatistik)

Preparation_and_transmetallation_of_a_triphenylstannyl_beta_D_glucopyranoside.pdf 98

Das Dokument erscheint in:

deposit-license Solange nicht anders angezeigt, wird die Lizenz wie folgt beschrieben: deposit-license

KOPS Suche


Stöbern

Mein Benutzerkonto