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Synthesis of 2-iodoglycals, glycals, and 1,1'-disaccharides from 2-Deoxy-2-iodopyranoses under dehydrative glycosylation conditions.
J Org Chem. 2007 Nov 09; 72(23):8998-9001.JO

Abstract

Treatment of 2-deoxy-2-iodopyranoses under dehydrative glycosylation conditions afforded pyranose glycals, 2-iodoglycals, and 1,1'-disaccharides instead of the expected glycoside products. While the product distribution revealed that this reaction is very sensitive to the configuration of the 2-deoxy-2-iodopyranose, 2-iodopyranoid glycals can be obtained almost exclusively in good yields by employing 3,4-O-isopropylidene as a cyclic bifunctional protecting group. The behavior of 2-deoxy-2-iodopyranoses during the dehydrative elimination reaction has been analyzed in detail.

Authors+Show Affiliations

Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel-lí Domingo s/n, 43007, Tarragona, Spain.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

17929873

Citation

Rodríguez, Miguel Angel, et al. "Synthesis of 2-iodoglycals, Glycals, and 1,1'-disaccharides From 2-Deoxy-2-iodopyranoses Under Dehydrative Glycosylation Conditions." The Journal of Organic Chemistry, vol. 72, no. 23, 2007, pp. 8998-9001.
Rodríguez MA, Boutureira O, Matheu MI, et al. Synthesis of 2-iodoglycals, glycals, and 1,1'-disaccharides from 2-Deoxy-2-iodopyranoses under dehydrative glycosylation conditions. J Org Chem. 2007;72(23):8998-9001.
Rodríguez, M. A., Boutureira, O., Matheu, M. I., Díaz, Y., Castillón, S., & Seeberger, P. H. (2007). Synthesis of 2-iodoglycals, glycals, and 1,1'-disaccharides from 2-Deoxy-2-iodopyranoses under dehydrative glycosylation conditions. The Journal of Organic Chemistry, 72(23), 8998-9001.
Rodríguez MA, et al. Synthesis of 2-iodoglycals, Glycals, and 1,1'-disaccharides From 2-Deoxy-2-iodopyranoses Under Dehydrative Glycosylation Conditions. J Org Chem. 2007 Nov 9;72(23):8998-9001. PubMed PMID: 17929873.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of 2-iodoglycals, glycals, and 1,1'-disaccharides from 2-Deoxy-2-iodopyranoses under dehydrative glycosylation conditions. AU - Rodríguez,Miguel Angel, AU - Boutureira,Omar, AU - Matheu,M Isabel, AU - Díaz,Yolanda, AU - Castillón,Sergio, AU - Seeberger,Peter H, Y1 - 2007/10/11/ PY - 2007/10/13/pubmed PY - 2008/1/8/medline PY - 2007/10/13/entrez SP - 8998 EP - 9001 JF - The Journal of organic chemistry JO - J. Org. Chem. VL - 72 IS - 23 N2 - Treatment of 2-deoxy-2-iodopyranoses under dehydrative glycosylation conditions afforded pyranose glycals, 2-iodoglycals, and 1,1'-disaccharides instead of the expected glycoside products. While the product distribution revealed that this reaction is very sensitive to the configuration of the 2-deoxy-2-iodopyranose, 2-iodopyranoid glycals can be obtained almost exclusively in good yields by employing 3,4-O-isopropylidene as a cyclic bifunctional protecting group. The behavior of 2-deoxy-2-iodopyranoses during the dehydrative elimination reaction has been analyzed in detail. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17929873/Synthesis_of_2_iodoglycals_glycals_and_11'_disaccharides_from_2_Deoxy_2_iodopyranoses_under_dehydrative_glycosylation_conditions_ L2 - https://dx.doi.org/10.1021/jo701738m DB - PRIME DP - Unbound Medicine ER -