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Neighboring group participation of 9-anthracenylmethyl group in glycosylation: preparation of unusual C-glycosides.
J Org Chem. 2005 Apr 01; 70(7):2808-11.JO

Abstract

[reaction: see text] A coupling of 2-O-arylmethylated D-glucose-derived thioglycosides with various alcohols in the presence of DMTST as an activator is described. The requisite glycosyl donors are efficiently prepared by one-pot procedures. When the aryl groups are phenyl, p-methoxyphenyl, 1-naphthyl, and 2-naphthyl groups, a mixture of alpha- and beta-anomeric O-glycosides is obtained under the conditions, whereas when the aryl group is the 9-anthracenyl group, a highly stereoselective formation of the unusual C-glycosides in good yields via neighboring group participation of the 9-anthracenylmethyl group followed by coupling with a variety of alcohols is observed. Three new chiral centers including a quaternary carbon are created in one single step.

Authors+Show Affiliations

Institute of Chemistry and Genomics Research Center, Academia Sinica, Taipei 115, Taiwan.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

15787575

Citation

Kulkarni, Suvarn S., et al. "Neighboring Group Participation of 9-anthracenylmethyl Group in Glycosylation: Preparation of Unusual C-glycosides." The Journal of Organic Chemistry, vol. 70, no. 7, 2005, pp. 2808-11.
Kulkarni SS, Liu YH, Hung SC. Neighboring group participation of 9-anthracenylmethyl group in glycosylation: preparation of unusual C-glycosides. J Org Chem. 2005;70(7):2808-11.
Kulkarni, S. S., Liu, Y. H., & Hung, S. C. (2005). Neighboring group participation of 9-anthracenylmethyl group in glycosylation: preparation of unusual C-glycosides. The Journal of Organic Chemistry, 70(7), 2808-11.
Kulkarni SS, Liu YH, Hung SC. Neighboring Group Participation of 9-anthracenylmethyl Group in Glycosylation: Preparation of Unusual C-glycosides. J Org Chem. 2005 Apr 1;70(7):2808-11. PubMed PMID: 15787575.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Neighboring group participation of 9-anthracenylmethyl group in glycosylation: preparation of unusual C-glycosides. AU - Kulkarni,Suvarn S, AU - Liu,Yi-Hung, AU - Hung,Shang-Cheng, PY - 2005/3/25/pubmed PY - 2005/5/18/medline PY - 2005/3/25/entrez SP - 2808 EP - 11 JF - The Journal of organic chemistry JO - J. Org. Chem. VL - 70 IS - 7 N2 - [reaction: see text] A coupling of 2-O-arylmethylated D-glucose-derived thioglycosides with various alcohols in the presence of DMTST as an activator is described. The requisite glycosyl donors are efficiently prepared by one-pot procedures. When the aryl groups are phenyl, p-methoxyphenyl, 1-naphthyl, and 2-naphthyl groups, a mixture of alpha- and beta-anomeric O-glycosides is obtained under the conditions, whereas when the aryl group is the 9-anthracenyl group, a highly stereoselective formation of the unusual C-glycosides in good yields via neighboring group participation of the 9-anthracenylmethyl group followed by coupling with a variety of alcohols is observed. Three new chiral centers including a quaternary carbon are created in one single step. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15787575/Neighboring_group_participation_of_9_anthracenylmethyl_group_in_glycosylation:_preparation_of_unusual_C_glycosides_ L2 - https://dx.doi.org/10.1021/jo047794a DB - PRIME DP - Unbound Medicine ER -
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