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Glycosides with phenylboronic acid

A study of the stability of compounds derived from D-glucose and D-fructose with boric acid or phenylboronic acid has found that the stability constants for the fructose compounds are much greater than those for the glucose compounds. The synthesis of crystalline 3-0-acetyl-2,4-0-phenylboranediyl- -D-ribopyranosyl bromide in a two pot process from D-ribose has been described along with some of its selective glycosylation reactions. Ethyl (dimethoxy)borane has been used in the synthesis of anomerically pure furanosides from the free sugars. Thus methyl 2,3-0-ethylboranediyl-tt-D-lyxofuranoside was prepared and then de-esterified under essentially neutral conditions to the glycoside in 80%... [Pg.189]

The stereoselectivity of the uncatalysed 0-1 methylation of free sugars with diazomethane has been correlated with the preferred conformations of the thermodynamically favoured anomers. More specific studies of methyl glycosides relate to the acid-catalysed methanolysis of a-D-glucofuranose 1,2 3,5-bis(phenylboronate), which gives the a- and 3-glucofuranosides in the ratio of... [Pg.13]

See other pages where Glycosides with phenylboronic acid is mentioned: [Pg.391]    [Pg.72]    [Pg.73]    [Pg.32]    [Pg.67]    [Pg.448]    [Pg.65]    [Pg.229]    [Pg.44]    [Pg.21]    [Pg.37]    [Pg.75]    [Pg.102]    [Pg.46]    [Pg.53]    [Pg.341]    [Pg.30]   
See also in sourсe #XX -- [ Pg.32 ]

See also in sourсe #XX -- [ Pg.32 , Pg.35 ]



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4- phenylboronic

Glycosidic acids

Phenylboronate

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