Investigation of acetyl migrations in furanosides

• O. P. Chevallier and
• M. E. Migaud

Beilstein J. Org. Chem. 2006, 2, No. 14, doi:10.1186/1860-5397-2-14

• O. P. Chevallier M. E. Migaud School of Chemistry and Chemical Engineering, Queen's University, David Keir Building, Stranmillis Road, Belfast, BT9 5AG, Northern Ireland, UK 10.1186/1860-5397-2-14 Abstract Standard reaction conditions for the desilylation of acetylated furanoside (riboside

• ribosides, acyl migration could be prevented when desilylation was catalysed by cerium ammonium nitrate. Introduction Over the years, a number of methods aimed at achieving chemoselective acylation of carbohydrates have been developed.[1][2][3] In addition to the challenges encountered in the selective

• experiments were sufficiently clear to allow accurate compound identification. No isomerisation was detected for any of the isolated compounds when stored in an organic solvent such as hexane, ethyl acetate or CDCl3 for up to 12 hrs. The chemical shifts of the 1H- and 13C-NMR of the desilylation products for

The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid

• Ishmael B. Masesane,
• Andrei S. Batsanov,
• Judith A. K. Howard,
• Raju Mondal and
• Patrick G. Steel

Beilstein J. Org. Chem. 2006, 2, No. 9, doi:10.1186/1860-5397-2-9

• failed. Fortunately, use of LiHMDS was successful albeit accompanied by the unexpected loss of Boc group. Similar strategies using either the free diol or the corresponding acetonide were not successful leading to extensive decomposition. Following TBAF promoted desilylation, peracylation and reduction

Synthesis of highly substituted allenylsilanes by alkylidenation of silylketenes

• Stephen P. Marsden and
• Pascal C. Ducept

Beilstein J. Org. Chem. 2005, 1, No. 5, doi:10.1186/1860-5397-1-5

• silylketenes with reactive ylides involves deprotonation by the basic reagent to generate ynolate anions. Clearly, since such a pathway cannot operate with the substituted ketenes used here other mechanisms are at play, which may include nucleophilic desilylation or ketene oligomerisation initiated by