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De novo asymmetric synthesis of an alpha-6-deoxyaltropyranoside as well as its 2-/3-deoxy and 2,3-dideoxy congeners.
J Org Chem. 2009 Aug 21; 74(16):5961-6.JO

Abstract

A highly divergent de novo asymmetric synthesis of benzyl alpha-6-deoxyaltropyranoside, benzyl alpha-ascarylopyranoside, benzyl alpha-amicetopyranoside, and benzyl alpha-digitoxopyranoside has been achieved via a common pyranone intermediate. The routes rely upon a palladium(0)-catalyzed glycosylation reaction and corresponding post-glycosylation transformations. The control of the absolute and relative stereochemical configuration came from a Noyori reduction of 2-acylfuran and subsequent diastereoselective introduction of other stereogenic centers.

Authors+Show Affiliations

Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

20560564

Citation

Shan, Mingde, et al. "De Novo Asymmetric Synthesis of an Alpha-6-deoxyaltropyranoside as Well as Its 2-/3-deoxy and 2,3-dideoxy Congeners." The Journal of Organic Chemistry, vol. 74, no. 16, 2009, pp. 5961-6.
Shan M, Xing Y, O'Doherty GA. De novo asymmetric synthesis of an alpha-6-deoxyaltropyranoside as well as its 2-/3-deoxy and 2,3-dideoxy congeners. J Org Chem. 2009;74(16):5961-6.
Shan, M., Xing, Y., & O'Doherty, G. A. (2009). De novo asymmetric synthesis of an alpha-6-deoxyaltropyranoside as well as its 2-/3-deoxy and 2,3-dideoxy congeners. The Journal of Organic Chemistry, 74(16), 5961-6. https://doi.org/10.1021/jo9009722
Shan M, Xing Y, O'Doherty GA. De Novo Asymmetric Synthesis of an Alpha-6-deoxyaltropyranoside as Well as Its 2-/3-deoxy and 2,3-dideoxy Congeners. J Org Chem. 2009 Aug 21;74(16):5961-6. PubMed PMID: 20560564.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - De novo asymmetric synthesis of an alpha-6-deoxyaltropyranoside as well as its 2-/3-deoxy and 2,3-dideoxy congeners. AU - Shan,Mingde, AU - Xing,Yalan, AU - O'Doherty,George A, PY - 2010/6/22/entrez PY - 2010/6/22/pubmed PY - 2010/10/5/medline SP - 5961 EP - 6 JF - The Journal of organic chemistry JO - J. Org. Chem. VL - 74 IS - 16 N2 - A highly divergent de novo asymmetric synthesis of benzyl alpha-6-deoxyaltropyranoside, benzyl alpha-ascarylopyranoside, benzyl alpha-amicetopyranoside, and benzyl alpha-digitoxopyranoside has been achieved via a common pyranone intermediate. The routes rely upon a palladium(0)-catalyzed glycosylation reaction and corresponding post-glycosylation transformations. The control of the absolute and relative stereochemical configuration came from a Noyori reduction of 2-acylfuran and subsequent diastereoselective introduction of other stereogenic centers. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20560564/De_novo_asymmetric_synthesis_of_an_alpha_6_deoxyaltropyranoside_as_well_as_its_2_/3_deoxy_and_23_dideoxy_congeners_ L2 - https://dx.doi.org/10.1021/jo9009722 DB - PRIME DP - Unbound Medicine ER -