Alkyl-p-D-glucopyranosides

Lu, W.-Y., Lin, G.-Q., Yu, H.-L. et al. (2007) Facile synthesis of alkyl p-D-glucopyranosides from D-glucose and the corresponding alcohols using fruit seed meals. Journal of Molecular Catalysis B Enzymatic, 44, 72-77. 

Ethylbenzene plants, 23 330-331 Ethylbenzene-styrene complex, 23 328 Ethylbenzene synthesis molecular sieves in, 16 845 zeolite-based alkylation in, 23 331-333 Ethyl benzoate, 3 635 Ethyl P-D-glucopyranoside, 4 701 7-Ethylbicyclooxazolidine, antimicrobial used in cosmetics, 7 831t Ethyl bromide, physical properties of, 4 351t... 

Table 7.3 Repeated alkyl fS-D-glucoside use 7.3 Facile Synthesis of Alkyl P-o-Glucopyranosides 237 ofP. dulcis kernel meal in the enzymatic synthesis of ... 

From methyl a-D-glucopyranoside, 55% of 2-O-benzyl and 18% of 3-O-benzyl derivatives could be obtained using 1,4-dioxane as a solvent. No monobenzyl derivative was observed under standard DMF solvent conditions [131]. Conformational equilibria 4Ct XC4 play a role in the results of alkylation of all-equatorial methyl P-D-xylopyranoside and methyl P-D-glucopyranoside [131]. 

Amino-2-deoxy-P-D-glucopyranosides. In the presence of Sn(OTf)2, 1,3,4,6-tetra-0-acetyl-2-deoxy-(2,2,2-trichloroethoxycarbonylamino)- 8-D-glucopyranose (1) reacts with alkyl trimethylsilyl ethers to form the corresponding -D-glucopyranosides 2 in >90% yield. This procedure is also applicable to preparation of )8-D-galactopyranosides. 

Physical studies on glycosides have included the X-ray diffraction analysis of methyl a-D-galactopyranosides and methyl p-D-glucopyranosides with fatty acid esters at C-6 which showed bilayer structures with zig-zag alkyl chains. The conformational behaviour of several non-ionisable lactose analogues have been examined by NMR and molecular mechanics methods, and the energy profile of methyl p-D-arabinofuranoside as a function of ring conformations has been determined by gas phase computations. ... 

High yields of p-D-ribofuranosides and P-D-glucopyranosides have been obtained by treating l-0-acetyl-2,3,5-tri-0-benzoyl-P-D-ribofuranose and p-o-glu-copyranose penta-acetate, respectively, in dichloromethane with equimolar quantities of an alcohol and tin(iv) chloride at or below room temperature. Several alkyl and cyclohexyl p-D-ribofuranosides were prepared by this method, which was extended to the synthesis of the protected disaccharide 6-0-(2,3,5-tri-0-benzoyl-P-D-ribofuranosyl)-l,2 3,4-di-0-isopropylidene-a-D-galactopyranose. Tin(iv) chloride also catalysed the formation of aryl p-D-ribofuranosides from P-D-ribofuranosyl tetra-acetate. An acetylated precursor has also been used in... 

Alkylation of metal chelates of sucrose with allyl halides and sodium bromo-acetate in DMSO yielded mono-O-allylated and mono-O-carboxymethylated derivatives. A new acidic monosaccharide from the O-specific lipopolysaccharide of Shigella dysenteriae type 3 has been identified as 4-0-[(/ )-l-carboxy-ethyl]-D-glucopyranose on the basis of chemical and mass-spectral evidence and by its synthesis by alkylation of methyl 2,3,6-tri-0-benzyl-a(P)-D-glucopyranoside with (5)-2-chloropropionic acid, esterification (with diazomethane), hydrogenolysis, and acid hydrolysis. ... 

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