A-Glucoheptose

Stacey started research in an inspiring and stimulating atmosphere that he strove to maintain, add to, and develop when it became his turn to lead the department. His earliest research was with Haworth and his key partner E. L. Hirst [Adv. Carbohydr. Chem. Biochem., 35 (1978) 1 -29] on aspects of the chemistry of glucoheptose. His first publication with them in 1931 was entitled Walden Inversion in the a-Glucoheptose Series, followed in the next year by a report on the methylation of monocarboxylic acids derived from aldoses and the structure of pentamethyl a-gluco-heptonolactone. He found this to be a difficult project because, initially, he could not crystallize his stock of glucoheptose. Then, as later, he found crystallization to be a challenging problem. 

On nitration it produces an expl compd d-a-Glucoheptose Hexonitrote,... 

Haworth, Hirst and Stacey showed that when either pentaacetyl-a-D-(o)-glucoheptosyl bromide or pentaacetyl-a-D-(a)-glucoheptosyl chloride, was refluxed for ten minutes in dry ether containing freshly prepared activated silver chloride, pentaacetyl-j3-n-(a)-glucoheptosyl chloride was obtained in almost quantitative yield. The transformations were somewhat capricious and their course could not always be predicted with certainty. The crystalline acetyl- -glycosyl chloride was heated for five hours at 70° with methyl alcohol and quinoline and maintained overnight at room temperature. Tetraacetyl-D-(a)-glucoheptose methyl... 

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