Efficient regioselective protection of myo-inositol via migration facile protecting group
2011 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 67, no 3, 618-623 p.Article in journal (Refereed) Published
A cis-1,2-cyclohexanediol, 1,4,5,6-tetra-O-benzyl-myo-inositol, was selectively protected at the axial C2-hydroxyl via acid-mediated rearrangement of the corresponding 1,2-orthoacetate, or via the base-induced migration of a protecting group that had previously been easily installed with complete regioselectivity at the adjacent equatorial hydroxyl. Esters 4a-6a were synthesized in high yields (75-82%) while sulfonate 7a and silyl ether 8a were obtained in 85 and 31% yields, respectively. The migration of the esters induced by DBU results in equilibrium between regioisomers favouring the C2 protected isomer, but NaH induced migration of sulfonyl and silyl groups results in complete migration from equatorial to axial hydroxyl groups.
Place, publisher, year, edition, pages
2011. Vol. 67, no 3, 618-623 p.
IdentifiersURN: urn:nbn:se:su:diva-67359DOI: 10.1016/j.tet.2010.11.063ISI: 000286862900008OAI: oai:DiVA.org:su-67359DiVA: diva2:470161
authorCount :72011-12-282011-12-282011-12-28Bibliographically approved