By W.W. Pigman, M.L. Wolfrom, Stanley Peat (Eds.)
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Extra resources for Advances in Carbohydrate Chemistry, Vol. 3
Fischer6 showed that mucic acid must be limited to one of these meso configurations, but a decision between them was not possible a t that time. The and - notations of this table are very confusing today because, as should be stated again for emphasis, the signs are given b y observing the tetrahedra ojthe mechanical model from a point within the model, namely, its center. It will be recalled that this convention was used b y Van’t Hoff for classifying the various tartaric acids; he extended the convention to the more complicated substances of the table, and it is in the consideration of them that one meets the following pitfall, as was described by Fischer in a supplementary articlesb sent in two months after dispatching his first article” on the configuration of glucose and its isomers.
1) The d and I symbols for configurations are not different from those that were in current use for rotations; (13) It seems to the writer that the names D-gluco-D-guh-heptose and D-gluco-Dido-heptose which he has suggested [C. S. Hudson, J . Am. Chem. , 80, 1537 (1938)] for the two glucoheptoses t h a t Fischer synthesized and named u-and &glucoheptose, are preferable to the designations D-glycero-D-gulo-heptose and D-glycero-D-ido-heptose which some chemists have substituted. The expansion of the old name D - ~ ~ U C O heptose by the introduction of the syllable D-gulo or D-idO to indicate the full configuration conforms to the general rules of organic nomenclature and k not the violation of them that has been inferred erroneously in some quarters.
When Haworth22and his coworkers discovered that the tetramethy1-Dglucose which results from the acid hydrolysis of either the a- or 0-anomer of fully methylated normal methyl glucoside is a 2,3,4,64etramethyl-~glucose, it became apparent that the oxygen bridge connects carbon atoms 1 and 5. In the abnormal or ‘‘ y ” type of glucoside this bridge was found to connect carbon atoms 1 and 4. Similar structures were disclosed in the fructose series, where the bridges were between carbon atoms 2 and 6 in the normal forms and between 2 and 5 in those of the “ y l l type.
Advances in Carbohydrate Chemistry, Vol. 3 by W.W. Pigman, M.L. Wolfrom, Stanley Peat (Eds.)