chapter  10
8 Pages

Stereoselective Reduction Using Sodium Triacetoxyborodeuteride: Synthesis of Methyl 2,3-Di-O-benzyl- α-d-(4-2H)-glucopyranoside

ByHani Mobarak, Olof Engström, Martina Lahmann, Göran Widmalm

Introduction .............................................................................................................. 82 General Methods ...................................................................................................... 82 Experimental Methods ............................................................................................. 83

Methyl 2,3-Di-O-benzyl-α-d-xylo-hexopyranosid-4-ulose (2) ........................... 83 Methyl 2,3-Di-O-benzyl-α-d-(4-2H)-glucopyranoside (3) .................................. 83

References ................................................................................................................87

Replacing a specic atom with an isotope has wide applications in chemistry, where it plays an important role in the elucidation of reaction mechanisms1 as well as tracing biological processes and unraveling biosynthetic routes in biochemistry.2,3 In these studies, mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy serve as important techniques in monitoring or revealing the information sought. Specically, isotope-labeled nucleic acids have been synthesized for use in MS,4 and specic labeling has been carried out to reduce spectral overlap, reveal specic nuclear spin-spin interactions, enhance the signal-to-noise ratio, or enable triple resonance experiments in NMR spectroscopy applications, resulting in compounds containing 2H,5-713C,8,915N,10 and 17O.11