Alkyl- -glucopyranosides

Alkyl glucopyranosides (alkyl is C, to C 2) can be prepared by direct acetalization of glucose with the appropriate alcohol under proton catalysis. Thus, in the case of 1-0-octyl glucoside the a-isomer can be easily and almost quantitatively obtained as its monohydrate by crystallization followed by recycling of the other product components. ... 

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. 

Methyl a-D-glucopyranoside may be converted,271 in a remarkably selective reaction, into its 2,4,6-tribenzyl ether (in 62% yield) on treatment with three molar equivalents of sodium hydride in benzyl chloride at 110°, a substitution pattern that might have been predicted in view of the low, relative reactivity of HO-3 towards alkylation in the mechanistically related, Haworth procedure.268 Similar, selective benzylations have also been achieved on partially substituted derivatives of methyl a- and /3-D-galactopyranoside272 and on methyl 6-deoxy-a-L-galactopyranoside62 in all of these, an unexpectedly high relative-reactivity of HO-4 (ax) compared to that of HO-3 (eq) was noted, indicating that steric factors are not the sole influence on reactivity in these cases. Nevertheless, the primary hydroxyl... 

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... 

The conformational anomeric effects design the contrasteric effects observed in acetals which render the more sterically encumbered gauche/ gauche conformers more stable than their anti/gauche and anti/anti conformers. Such effects were first evidenced by Jungins in 1905 and rediscovered by Edward in 1955 and by Lemieux and Chiu in 1958. They observed the higher stability of alkyl a-D-glucopyranosides in comparison with their (3-anomers (Fig. 5).8... 

In (+)-ionisation mode, a distinct selectivity of monoglucosides with respect to the formation of adduct ions was observed. Depending on the ring form (glucopyranoside or glucofuranoside) and the stereoisomerism (a- or (3-alkyl monoglucoside), a different affinity towards Na+ and... 

Fig. 5.1.20. Possible degradation pathways of alkyl glucopyranosides n = 8,10,12,14,16 (taken from Ref. [39]). by Elsevier, 1999.

Facile Synthesis of Alkyl y0-D-Glucopyranosides from o-Glucose and the Corresponding Alcohols Using Fruit Seed Meals... 

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 ... 

We have developed some novel, cheap, and green biocatalysts for the facile synthesis of various alkyl /3-D-glucopyranosides. Those easily available biocatalysts enable large-scale preparation of physiologically active /3-D-glucopyranosides (H.L. Yu, J.H. Xu, W.Y. Lu and G.Q. Lin, unpublished results). 

Takeo, K. Shibata, K., Regioselective Alkylation, Benzoylation, and Para-Toluene Sulfonylation of Methyl 4,6-0-Benzylidene-Beta-D-Glucopyranoside. Carbohydr. 

Jenkins, D. J. Potter, B. V. L., On the Selectivity of Stannylene-Mediated Alkylation and Esterification of Methyl 4,6-O-Benzylidene Alpha-D-Glucopyranoside. 

Aldicarb nitrile, see Aldicarb Aldicarb nitrile sulfone, see Aldicarb Aldicarb nitrile sulfoxide, see Aldicarb Aldicarb oxime, see Aldicarb Aldicarb oxime sulfone, see Aldicarb Aldicarb oxime sulfoxide, see Aldicarb Aldicarb sulfone, see Aldicarb Aldicarb sulfone acid, see Aldicarb Aldicarb sulfone alcohol, see Aldicarb Aldicarb sulfone aldehyde, see Aldicarb Aldicarb sulfone amide, see Aldicarb Aldicarb sulfone oxime, see Aldicarb Aldicarb sulfoxide, see Aldicarb Aldicarb sulfoxide acid, see Aldicarb Aldicarb sulfoxide alcohol, see Aldicarb Aldicarb sulfoxide aldehyde, see Aldicarb Aldicarb sulfoxide amide, see Aldicarb Aldicarb sulfoxide nitrile, see Aldicarb Aldicarb sulfoxide oxime, see Aldicarb Aldrin, see Dieldrin Aldrin diol, see Aldrin Alkyl hydroperoxides, see Acetaldehyde Allyl alcohol, see Allyl chloride, l,2-Dibromo-3-chloropropane, 1,2-Dichloropropane Allylbenzene, see Isopropylbenzene p-(2-Atnino-3-nitrophenyl)glucopyranoside, see 2-Nitroaniline Allyl chloride, see Allyl alcohol, l,2-Dibromo-3-chloropropane, 1,2-Dichloropropane 2-Aminobenzimidazole, see Benomvl... 

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