A Facile Synthesis of Benzyl 2-Amino-3-azido-4-O-p-methoxybenzyl-6-O-benzyl-2,3-dideoxy-α-d-glucopyranoside: A Key Intermediate in the Formation Of A Didemnin B Analog

Abstract

Although the deprotection of amides by hydrazinolysis is a well established method in carbohydrate chemistry, this reaction is dependent upon the nearby substituents. In our facile synthesis of intermediate benzyl 2-amino-3-azido-4-O-p-methoxybenzyl-6-O-benzyl-2,3-dideoxy-α-d-glucopyranoside (3), we found that the use of trifluoroacetamides provided a more efficient protection strategy.

Notes

The X-ray structure of compound 13 has been submitted for publication to Acta Crystallogr., Section C. Suitable crystals were obtained using vapor diffusion techniques with ethyl acetate/hexane as the solvent pair under nitrogen atmosphere. X-ray intensity data were collected on a Rigaku R-AXIS-IIc area detector employing graphite-monochromated Mo-Kα radiation (λ = 0.71069 Å). The structure was solved and refined using the Molecular Structure Corporation teXsan package on a Silicon Graphics R4000 computer.