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Stereoselective synthesis of 2-deoxy-beta-galactosides via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl donors.
Org Lett. 2003 May 29; 5(11):1871-4.OL

Abstract

[reaction: see text] A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors.

Authors+Show Affiliations

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

12762674

Citation

Durham, Timothy B., and William R. Roush. "Stereoselective Synthesis of 2-deoxy-beta-galactosides Via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl Donors." Organic Letters, vol. 5, no. 11, 2003, pp. 1871-4.
Durham TB, Roush WR. Stereoselective synthesis of 2-deoxy-beta-galactosides via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl donors. Org Lett. 2003;5(11):1871-4.
Durham, T. B., & Roush, W. R. (2003). Stereoselective synthesis of 2-deoxy-beta-galactosides via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl donors. Organic Letters, 5(11), 1871-4.
Durham TB, Roush WR. Stereoselective Synthesis of 2-deoxy-beta-galactosides Via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl Donors. Org Lett. 2003 May 29;5(11):1871-4. PubMed PMID: 12762674.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective synthesis of 2-deoxy-beta-galactosides via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl donors. AU - Durham,Timothy B, AU - Roush,William R, PY - 2003/5/24/pubmed PY - 2003/9/10/medline PY - 2003/5/24/entrez SP - 1871 EP - 4 JF - Organic letters JO - Org. Lett. VL - 5 IS - 11 N2 - [reaction: see text] A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/12762674/Stereoselective_synthesis_of_2_deoxy_beta_galactosides_via_2_deoxy_2_bromo__and_2_deoxy_2_iodo_galactopyranosyl_donors_ L2 - https://dx.doi.org/10.1021/ol034393t DB - PRIME DP - Unbound Medicine ER -