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Synthesis and intramolecular transesterifications of pivaloylated methyl alpha-D-galactopyranosides.
Carbohydr Res 2002; 337(9):863-7CR

Abstract

Selective pivaloylations of methyl alpha-D-galactopyranoside have been studied under various reaction conditions. Partially pivaloylated products were submitted to additional acetylations. The structures were established by 1H and 13C NMR spectroscopies. Both, 2,6- and 3,6-dipivalates underwent intramolecular cyclization in neutral conditions (phosphate buffered saline, pH 7.2) to give a stable 2,3-orthoacid with a parallel 6-->4 migration of the pivaloyl group.

Authors+Show Affiliations

Department of Chemistry, Faculty of Science, University of Zagreb, Strossmayerov trg 14, Croatia.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

11996840

Citation

Petrović, Vesna, et al. "Synthesis and Intramolecular Transesterifications of Pivaloylated Methyl Alpha-D-galactopyranosides." Carbohydrate Research, vol. 337, no. 9, 2002, pp. 863-7.
Petrović V, Tomić S, Matanović M. Synthesis and intramolecular transesterifications of pivaloylated methyl alpha-D-galactopyranosides. Carbohydr Res. 2002;337(9):863-7.
Petrović, V., Tomić, S., & Matanović, M. (2002). Synthesis and intramolecular transesterifications of pivaloylated methyl alpha-D-galactopyranosides. Carbohydrate Research, 337(9), pp. 863-7.
Petrović V, Tomić S, Matanović M. Synthesis and Intramolecular Transesterifications of Pivaloylated Methyl Alpha-D-galactopyranosides. Carbohydr Res. 2002 Apr 30;337(9):863-7. PubMed PMID: 11996840.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and intramolecular transesterifications of pivaloylated methyl alpha-D-galactopyranosides. AU - Petrović,Vesna, AU - Tomić,Srdanka, AU - Matanović,Maja, PY - 2002/5/9/pubmed PY - 2002/12/18/medline PY - 2002/5/9/entrez SP - 863 EP - 7 JF - Carbohydrate research JO - Carbohydr. Res. VL - 337 IS - 9 N2 - Selective pivaloylations of methyl alpha-D-galactopyranoside have been studied under various reaction conditions. Partially pivaloylated products were submitted to additional acetylations. The structures were established by 1H and 13C NMR spectroscopies. Both, 2,6- and 3,6-dipivalates underwent intramolecular cyclization in neutral conditions (phosphate buffered saline, pH 7.2) to give a stable 2,3-orthoacid with a parallel 6-->4 migration of the pivaloyl group. SN - 0008-6215 UR - https://www.unboundmedicine.com/medline/citation/11996840/Synthesis_and_intramolecular_transesterifications_of_pivaloylated_methyl_alpha-D-galactopyranosides L2 - https://linkinghub.elsevier.com/retrieve/pii/S0008621502000551 DB - PRIME DP - Unbound Medicine ER -