2-Furaldehyde 5-methoxymethyl

AW, Acid-washed Choi, Cholesterol DMAP, 4-(Dimethylamino)pyridine DMF, N,/V-Dimethylformamide DMTr, Di(p-niethoxyphenyl)phenyl methyl GalNAc, N-Acetylgalactosamine, 2-acetamido-2-deoxy-D-galactose HMF, 5-Hydroxymethylfur-fural, 5-(hydroxymethyl)-2-furaldehyde INOC, Intramolecular nitrile oxide-alkene cycloaddition Lea, Lewisa Lex, Lewisx MOM, Methoxymethyl MP, p-Methoxyphe-nyl MS, Molecular sieves NIS, N-Iodosuccinimide PCC, Pyridinium chlorochromate PDC, Pyridinium dichromate PMA, Phosphomolybdic acid PMB, p-Methoxybenzyl ... 

The 2-hydroxyglycals provide additional source material for the study of dismutation reactions, the reaction of the acyl derivatives of the hexoses climaxing in di-O-acetylkojic acid or di-O-benzoylkojic acid through loss of acetic or benzoic acid and of the O-methyl derivatives in 5-(methoxymethyl)-2-furaldehyde through loss of methanol. The formation of the 2-hydroxyglycals as intermediates in the reaction of some alkalis on sugars has been proposed by Kusin8 in an effort to explain the cationic dependence exhibited by the products. His mechanism has not, however, been established. 

On interruption of the reaction at the minimum point, only a low yield of the final product, 5-(methoxymethyl)-2-furaldehyde, could be isolated as the semicarbazone, but a crystalline phenylosazone (m.p. 120.5-121.5°, [< ]d —9° in chloroform) was obtained. It was not isolable at the end of the reaction. No osazone was obtainable from the hydroxy-glycal without prior, acid treatment. Analyses of the osazone indicated that it was a mono-O-methyl derivative of the parent CgHgCh. This is the same formula that was found by Bergmann and Zervas (see above ) for the parent of the phenylosazone obtained by direct treatment of 2,3,4,6-tetra-0-acetyl-(2-hydroxy-D-glucal) with phenylhydrazine. Whereas Bergmann and Zervas were unable to acetylate the compound further, Wolfrom, Wallace and Metcalf introduced an O-acetyl group into their mono-O-... 

The glycosulos-3-enes are theoretically derived from a 3-deoxyglycosulose by the loss of one molecule of water per molecule. A compound of this type, (32), was first isolated as the phenylosazone by Wolfrom, Wallace, and Metcalf, and was shown to be an intermediate in the conversion of 1-deoxy-tetra-O-methyl-D-orobtno-hexopyranos-l-ene (31) (tetra-O-methyl-n-glucoseen-1,2) to 5-(methoxymethyl)-2-furaldehyde (33). The evidence... 

Podesta, F., Fajardo, V., Freyer, A.J., Shamma, M., 1988. 5-Methoxymethyl-2-furaldehyde a Natural Furanoid from Jabomsa Magellanica (Solanaceae) 5-Methoxymethyl-furfural ein natiirliches Furanoid aus ]aborosa mugellunica (Colanaceae). Archiv der Pharmazie 321,949. 

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