We have developed a synthetic route to the frequently utilized deoxysugar building block di-O-acetyl-D-rhamnal originating from the inexpensive starting material methyl α-D-glucopyranoside. Our approach proceeds in five steps with minimal column chromatography purification needed to afford the title compound in good overall yield. 2009 Elsevier Ltd. All rights reserved.

Synthesis of Functionalized Fluorescent Dyes and Their Coupling toAmines and Amino Acids.-A series of novel functionalized benzophenoxazinones (cf. (III), (V), ( VI)), analogues of Nile Red, is synthesized and evaluated for their fluorescence properties. In order to allow labeling of proteins and other biomolecules, the carboxylic acid (VI) is coupled to a range of amino compounds (→ (X), (XII)). -(BRIGGS, M. S. J.; BRUCE, I.; MILLER, J. N.; MOODY, C. J.; SIMMONDS, A. C.; SWANN, E.; J.

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The use of the Mitsunobu reaction for the synthesis of N,N-diethylbenzamides affords ortho-, meta-, and para-substituted benzamides, containing both electron-donating and electron-withdrawing groups. While the preparation of numerous functional groups has been efficiently demonstrated employing the Mitsunobu reaction, our methodology represents the first application of the Mitsunobu reaction for the construction of benzamides using benzoic acid and amine starting materials. Moreover, this synthetic transformation is believed to proceed via a non-classical mechanism involving the existence of an acyloxyphosphonium ion.

Synthesis of N,N-Diethylbenzamides via a Nonclassical Mitsunobu Reaction. -The first application of the Mitsunobu reaction for the construction of benzamides from various benzoic acids and amine is presented. -(HOFFMAN, J. M.; MILLER, J. N.; GARDNER, M. E.; LEPAR, D. R.; PONGDEE*, R.; Synth. Commun. 44 (2014) 7, 976-980, http://dx.