Tags

Type your tag names separated by a space and hit enter

Oxidant-controlled heck-type C-glycosylation of glycals with arylboronic acids: stereoselective synthesis of aryl 2-deoxy-C-glycosides.
Org Lett. 2009 Apr 16; 11(8):1709-12.OL

Abstract

Oxidative Heck-type C-glycosylations of glycals with various arylboronic acids using Pd(OAc)(2) as catalyst in the presence of oxidant were developed. The corresponding ketone, enol ether, and enone types of C-glycosides were predictably obtained with benzoquinone (BQ), Cu(OAc)(2)/O(2), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidants, respectively. This method provides a simple, mild, and stereoselective synthesis of aryl 2-deoxy-C-glycosides.

Authors+Show Affiliations

State Key Laboratory of Natural and Biomimetic Drugs, Peking University, and School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd No. 38, Beijing 100191, China.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

19301870

Citation

Xiong, De-Cai, et al. "Oxidant-controlled Heck-type C-glycosylation of Glycals With Arylboronic Acids: Stereoselective Synthesis of Aryl 2-deoxy-C-glycosides." Organic Letters, vol. 11, no. 8, 2009, pp. 1709-12.
Xiong DC, Zhang LH, Ye XS. Oxidant-controlled heck-type C-glycosylation of glycals with arylboronic acids: stereoselective synthesis of aryl 2-deoxy-C-glycosides. Org Lett. 2009;11(8):1709-12.
Xiong, D. C., Zhang, L. H., & Ye, X. S. (2009). Oxidant-controlled heck-type C-glycosylation of glycals with arylboronic acids: stereoselective synthesis of aryl 2-deoxy-C-glycosides. Organic Letters, 11(8), 1709-12. https://doi.org/10.1021/ol900273d
Xiong DC, Zhang LH, Ye XS. Oxidant-controlled Heck-type C-glycosylation of Glycals With Arylboronic Acids: Stereoselective Synthesis of Aryl 2-deoxy-C-glycosides. Org Lett. 2009 Apr 16;11(8):1709-12. PubMed PMID: 19301870.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Oxidant-controlled heck-type C-glycosylation of glycals with arylboronic acids: stereoselective synthesis of aryl 2-deoxy-C-glycosides. AU - Xiong,De-Cai, AU - Zhang,Li-He, AU - Ye,Xin-Shan, PY - 2009/3/24/entrez PY - 2009/3/24/pubmed PY - 2009/5/2/medline SP - 1709 EP - 12 JF - Organic letters JO - Org. Lett. VL - 11 IS - 8 N2 - Oxidative Heck-type C-glycosylations of glycals with various arylboronic acids using Pd(OAc)(2) as catalyst in the presence of oxidant were developed. The corresponding ketone, enol ether, and enone types of C-glycosides were predictably obtained with benzoquinone (BQ), Cu(OAc)(2)/O(2), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidants, respectively. This method provides a simple, mild, and stereoselective synthesis of aryl 2-deoxy-C-glycosides. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19301870/Oxidant_controlled_heck_type_C_glycosylation_of_glycals_with_arylboronic_acids:_stereoselective_synthesis_of_aryl_2_deoxy_C_glycosides_ L2 - https://dx.doi.org/10.1021/ol900273d DB - PRIME DP - Unbound Medicine ER -