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Synthesis of 2-iodo-2-deoxy septanosides from a D-xylose-based oxepine: intramolecular cyclization in the absence of a glycosyl acceptor.
Carbohydr Res. 2004 Oct 04; 339(14):2363-70.CR

Abstract

Oxidative glycosylations of the D-xylose-based oxepine 1,6-anhydro-3,4,5-tri-O-benzyl-2-deoxy-D-xylosept-1-enitol (1) using N-iodosuccinimide (NIS) are reported. The reaction produced 2-deoxy-2-iodo-alpha-D-idoseptanosides and 2-deoxy-2-iodo-beta-D-guloseptanosides 2-9 in good yields. When limited equivalents of a glycosyl acceptor were used, or in the absence of a glycosyl acceptor, an intramolecular cyclization predominated to form 1,6-anhydro-3,4-di-O-benzyl-2-deoxy-2-iodo-alpha-D-idopyranose (10).

Authors+Show Affiliations

Department of Chemistry, The University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269, USA.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15388351

Citation

Fyvie, W Sean, et al. "Synthesis of 2-iodo-2-deoxy Septanosides From a D-xylose-based Oxepine: Intramolecular Cyclization in the Absence of a Glycosyl Acceptor." Carbohydrate Research, vol. 339, no. 14, 2004, pp. 2363-70.
Fyvie WS, Morton M, Peczuh MW. Synthesis of 2-iodo-2-deoxy septanosides from a D-xylose-based oxepine: intramolecular cyclization in the absence of a glycosyl acceptor. Carbohydr Res. 2004;339(14):2363-70.
Fyvie, W. S., Morton, M., & Peczuh, M. W. (2004). Synthesis of 2-iodo-2-deoxy septanosides from a D-xylose-based oxepine: intramolecular cyclization in the absence of a glycosyl acceptor. Carbohydrate Research, 339(14), 2363-70.
Fyvie WS, Morton M, Peczuh MW. Synthesis of 2-iodo-2-deoxy Septanosides From a D-xylose-based Oxepine: Intramolecular Cyclization in the Absence of a Glycosyl Acceptor. Carbohydr Res. 2004 Oct 4;339(14):2363-70. PubMed PMID: 15388351.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of 2-iodo-2-deoxy septanosides from a D-xylose-based oxepine: intramolecular cyclization in the absence of a glycosyl acceptor. AU - Fyvie,W Sean, AU - Morton,Martha, AU - Peczuh,Mark W, PY - 2004/07/12/received PY - 2004/07/14/revised PY - 2004/07/15/accepted PY - 2004/9/25/pubmed PY - 2005/3/30/medline PY - 2004/9/25/entrez SP - 2363 EP - 70 JF - Carbohydrate research JO - Carbohydr. Res. VL - 339 IS - 14 N2 - Oxidative glycosylations of the D-xylose-based oxepine 1,6-anhydro-3,4,5-tri-O-benzyl-2-deoxy-D-xylosept-1-enitol (1) using N-iodosuccinimide (NIS) are reported. The reaction produced 2-deoxy-2-iodo-alpha-D-idoseptanosides and 2-deoxy-2-iodo-beta-D-guloseptanosides 2-9 in good yields. When limited equivalents of a glycosyl acceptor were used, or in the absence of a glycosyl acceptor, an intramolecular cyclization predominated to form 1,6-anhydro-3,4-di-O-benzyl-2-deoxy-2-iodo-alpha-D-idopyranose (10). SN - 0008-6215 UR - https://www.unboundmedicine.com/medline/citation/15388351/Synthesis_of_2_iodo_2_deoxy_septanosides_from_a_D_xylose_based_oxepine:_intramolecular_cyclization_in_the_absence_of_a_glycosyl_acceptor_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0008-6215(04)00313-1 DB - PRIME DP - Unbound Medicine ER -