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Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C6F5)3 as Catalyst.
J Org Chem. 2019 03 01; 84(5):2415-2424.JO

Abstract

B(C6F5)3 enables the metal-free unprecedented substrate-controlled direct α-stereoselective synthesis of deoxyglycosides from glycals. 2,3-Unsaturated α- O-glycoside products are obtained with deactivated glycals at 75 °C in the presence of the catalyst, while 2-deoxyglycosides are formed using activated glycals that bear no leaving group at C-3 at lower temperatures. The reaction proceeds in good to excellent yields via concomitant borane activation of glycal donor and nucleophile acceptor. The method is exemplified with the synthesis of a series of rare and biologically relevant glycoside analogues.

Authors+Show Affiliations

School of Chemistry , University of Bristol , Cantock's Close, Bristol BS8 1TS , United Kingdom.School of Chemistry , University of Bristol , Cantock's Close, Bristol BS8 1TS , United Kingdom.School of Chemistry , University of Bristol , Cantock's Close, Bristol BS8 1TS , United Kingdom.

Pub Type(s)

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

Language

eng

PubMed ID

30706711

Citation

Sau, Abhijit, et al. "Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides From Glycals Using B(C6F5)3 as Catalyst." The Journal of Organic Chemistry, vol. 84, no. 5, 2019, pp. 2415-2424.
Sau A, Palo-Nieto C, Galan MC. Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C6F5)3 as Catalyst. J Org Chem. 2019;84(5):2415-2424.
Sau, A., Palo-Nieto, C., & Galan, M. C. (2019). Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C6F5)3 as Catalyst. The Journal of Organic Chemistry, 84(5), 2415-2424. https://doi.org/10.1021/acs.joc.8b02613
Sau A, Palo-Nieto C, Galan MC. Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides From Glycals Using B(C6F5)3 as Catalyst. J Org Chem. 2019 03 1;84(5):2415-2424. PubMed PMID: 30706711.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C6F5)3 as Catalyst. AU - Sau,Abhijit, AU - Palo-Nieto,Carlos, AU - Galan,M Carmen, Y1 - 2019/02/15/ PY - 2019/2/2/pubmed PY - 2020/5/2/medline PY - 2019/2/2/entrez SP - 2415 EP - 2424 JF - The Journal of organic chemistry JO - J. Org. Chem. VL - 84 IS - 5 N2 - B(C6F5)3 enables the metal-free unprecedented substrate-controlled direct α-stereoselective synthesis of deoxyglycosides from glycals. 2,3-Unsaturated α- O-glycoside products are obtained with deactivated glycals at 75 °C in the presence of the catalyst, while 2-deoxyglycosides are formed using activated glycals that bear no leaving group at C-3 at lower temperatures. The reaction proceeds in good to excellent yields via concomitant borane activation of glycal donor and nucleophile acceptor. The method is exemplified with the synthesis of a series of rare and biologically relevant glycoside analogues. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/30706711/Substrate_Controlled_Direct_α_Stereoselective_Synthesis_of_Deoxyglycosides_from_Glycals_Using_B_C6F5_3_as_Catalyst_ L2 - https://dx.doi.org/10.1021/acs.joc.8b02613 DB - PRIME DP - Unbound Medicine ER -