SOME OPEN-CHAIN DERIVATIVES OF GLUCOSE AND MANNOSE

1960 ◽  
Vol 38 (6) ◽  
pp. 890-895 ◽  
Author(s):  
E. J. C. Curtis ◽  
J. K. N. Jones

The dimethyl thioacetals of D-glucose and D-mannose have been condensed with acetone. Mannose dimethyl thioacetal forms a crystalline 3,4:5,6-di-O-isopropylidene derivative while glucose forms a mixture of the crystalline 3,4:5,6-di-O-isopropylidene and syrupy 2,3:5,6-di-O-isopropylidene isomers. These three di-O-isopropylidene dimethyl thioacetals have been converted via crystalline intermediates into the corresponding di-O-isopropylidene dimethyl acetals. These derivatives are suitable open-chain compounds for use in Koenigs–Knorr syntheses and provide (a) mannose with the C2 hydroxyl free, (b) glucose with the C2 hydroxyl free, and (c) glucose with the C4 hydroxyl free.

1959 ◽  
Vol 81 (7) ◽  
pp. 1729-1734 ◽  
Author(s):  
Leonidas Zervas ◽  
Leo Benoiton ◽  
Ellinor Weiss ◽  
Milton Winitz ◽  
Jesse P. Greenstein

1977 ◽  
Vol 30 (10) ◽  
pp. 2255 ◽  
Author(s):  
N Latif ◽  
N Mishriky ◽  
M Hammad

Cyano(fluoren-9-yl)acetohydrazides cyclize readily under acid or basic conditions to give 3-amino-4-(9-substituted fluoren-9-yl)pyrazol-5(4H)- ones (3). Upon thermolysis of the hydrazides the pyrazolones and/or dimeric products are produced.��� The cyanoacetohydrazides condense with phthalic anhydride to give the 2-(fluoren-9-yl)-N-phthalimidoacetamides(7), whereas, with succinic anhydride, the open-chain compounds (10) are obtained which upon thermolysis afford the dimeric compounds (6). The acetamides (7) undergo unusual reductive cleavage with sodium borohydride affording the fluorenylpyrazolones (3). Electronic, infrared and N.M.R. spectra of the products are discussed.


1934 ◽  
Vol 11 (3) ◽  
pp. 382-394 ◽  
Author(s):  
C. F. H. Allen ◽  
J. B. Normington ◽  
C. V. Wilson

A considerable number of highly substituted acrylic acids or their lactols have been synthesized, and the Grignard reagent used to differentiate between the two possible structures. Acetyl chloride was found to be a satisfactory confirmatory agent, giving chlorides with the lactols, but not reacting with the open-chain acids. From the available evidence it is concluded that the differences may be attributed to cis-trans isomerism.Two other series of ketonic acids were investigated with both reagents; the Grignard reagent indicated mostly open-chain structures. The use of acetyl chloride led to a variety of products; by varying the procedure, dimers of undetermined structure, unsaturated lactones, enolic acetates, and methyl esters were obtained.Cyclohexanone gave cyclohexenyl acetate with acetyl chloride.The mechanism of the reactions is discussed, as well as the evidence for the possible structures of derivatives of levulinic acid. A mechanism is suggested to account for the formation of enolic esters and unsaturated lactones of enolized ketonic acids.


ChemInform ◽  
2010 ◽  
Vol 28 (29) ◽  
pp. no-no ◽  
Author(s):  
A. TSOTINIS ◽  
A. VARVARESOU ◽  
T. CALOGEROPOULOU ◽  
T. SIATRA-PAPASTAIKOUDI ◽  
A. TILIGADA

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