A-Glucose pentaacetate

Penta-O-acetyl-a/de/iycfo-D-glucose 2,4-Di-0-acetyl-6-0-trityl-D-glucopyranose or a/dehydo-D-glucose pentaacetate... 

Cellobiose Octaacetate and Glucose Pentaacetate. Eastman White Label materials were purified by recrystallization from a methylene chloride-methanol mixture. 

Glucose pentaacetate and cellobiose octaacetate also yielded a fraction which was insoluble in methylene chloride and which appeared polymeric and amorphous. 

Comparative investigations with related monomeric compounds, glucose pentaacetate, and cellobiose octaacetate indicate that, on a qualitative basis, these materials undergo photolytic changes in a manner similar to cellulose triacetate. These materials may serve as model compounds for future quantitative investigations of cellulose triacetate. 

Also, the Ai peak (m/e 331) in the spectrum of a-D-glucose pentaacetate (12) is more intense than in that of the 0-d anomer (9). 

A classical selective reaction, described by Fischer and Armstrong,166 in which 6-bromo-6-deoxy-2,3,4-tri-0-acetyl-a-D-glucopyranosyl bromide (LXXXIX) is obtained from 0-D-glucose pentaacetate and liquid hydrogen bromide, has had application in the synthesis of 6-substituted D-glucose derivatives. The action of liquid hydrogen chloride on D-glu-cose has been studied by Hess, Strieker and Rutkowski,168 who have postulated a 1,1-chlorohydrin (XC) as an initial intermediate of the reaction. 

To obtain the ethylene oxide type compound, /3-D-glucose pentaacetate was treated with an excess of phosphorus pentachloride to give 2-tri-chloroacetyl-3,4,6-triacetyl-/3-D-glucopyranosyl chloride.63,63a The tri-chloroacetyl group was removed by treatment with a dry ethereal solution of ammonia at 0°. From the product the anhydride may be obtained by... 

In all of these processes, it is not clear whether the aluminum chloride, the phosphorus pentachloride, or both are the primary chlorinating agents. While phosphorus pentachloride alone in chloroform has been reported9 to produce tetraacetyl-a-D-fructosyl chloride from /3-D-fructose pentaacetate, its action on /3-D-glucose pentaacetate in the absence of... 

FRACTION OF THEORETICAL QUANTITY OF CATALYST Fig. 1. Product Yields as a Function of Catalyst Quantity in the Glucosylation of Benzene with 0-D-Glucose Pentaacetate. 

Niemann and Hays later showed that the oxidation of one mole of iV-acetyl-D-glucosylamine by lead tetraacetate involves the slow consumption of slightly more than two moles of oxidant, so confirming the result of periodate oxidation. Hockett and Chandler prepared an isomeric N-acetyl-D-glucosylamine, also cyclic since it gives a tetraacetate, by the action of 29 % aqueous ammonia on aldehydo-D-glucose pentaacetate or on hexa-0-acetyl- a -D-glucoheptonic nitrile. The oxidation of this isomer produced formaldehyde (isolated as its 2,4-dinitrophenylhydrazone), but... 

Dickey and Wolfrom separated a cellulose acetolyzate into a polymer-homologous series of crystalline sugar acetates complete from a-D-glucose pentaacetate through a-cellohexaose eicosaacetate by the application of chromatographic procedures. 

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