Productive protonation, glycosides

The anomeric proton in phenylthio 2,3-dideoxy-hex-2-enopyranosides is sufficiently acidic to enable deprotonation and, for example, reaction of S-glyco-side 68 with BuLi leads to dianion 69 which alkylates or acylates at C (1) from the a-face to give C-glycosides 70 (Scheme 17) [24]. Similarly, deprotonation of hex-2-enopyranoside 71 and coupling with cyclic sulfate 72 provides alkylated product 73 which, upon hydrolysis at pH > 3.5, undergoes a loss of sulfate and a... 

The sole Nano-probe paper published in 2004 of which the author is aware was the study by Claeyssens and co-workers220 of the enzymatic hydrolysis products of Nothogenia erinacea seaweed xylan, which is a linear homopolymer with mixed / — (1 —3)// — (1 —4) linkages. The sequence of the residues was determined from a combination of nuclear overhauser effect spectroscopy (NOESY) correlations between the anomeric protons and a proton of the residue to which it is glycosidically linked and gHMBC data, that were acquired using Nano-probe capabilities. Finally, in early 2005, Bradley et al.221 compared the ability of cryogenic, Nano- and conventional NMR probes to acquire diffusion-ordered spectroscopy (DOSY) spectra of dilute mixtures of compounds. 

---