234. Acetone derivatives of methylglycosides

Ault, R. G.; Haworth, Walter Norman; Hirst, E. L.

doi:10.1039/jr9350001012

Cited by 32 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus trim ethyl 1,4-anhydroglucopyranose [34] requires the conformation of a boat-shaped ring in which carbons 1 and 4 lie in the trough. The model which will serve for this compound, however, will not serve for 2,3-4,6-diacetone a-methyl mannopyranoside [35], because in order to form a 1,4-anhydro derivative the hydroxyl on carbon 4 (which is the same for mannose and glucose) must be directed towards carbon 1 which is in opposition to carbon 6. It is thus apparent that the conformation of the pyranose ring is not the same for all sugar derivatives.…”

Section: Conformation Of the Pyranose Ringmentioning

confidence: 99%

Configuration of the pyranoses in relation to their properties and nomenclature

Isbell¹

1937

J. RES. NATL. BUR. STAN.

View full text Add to dashboard Cite

Optical rotation, mutarotation, and bromine oxidation measurements are reported for seven heptoses. The results reveal striking similarity in the properties of the sugars classified in the following groups: (1) The structural characteristics of the alpha and beta sugars are discussed in relation to their reactions and their nomenclature. The rates of reaction and other properties indicate that there is an important structural difference in the alpha and beta sugars. This difference is in accord with the concept that the pyranose ring is of the strainless multiplanar type rather than monoplanar. The application of Hudson's rule for selecting the alpha and beta names is considered, and it is suggested that an additional criterion be added to this rule in order to obtain a nomenclature for the carbohydrates and their derivatives, based on the most fundamental structural properties in relation to the optical rotations, together with the theory of optical superposition. Comparisons of the optical rotations of the hexose sugars give values for the rotational differences which may be grouped according to the configurations of the neighboring atoms. The rotational differences obtained from substances of similar or related configuration agreej the rotational differences obtained by the comparison of substances of widely different configuration are not in agreement. CONTENTS

show abstract

Section: Conformation Of the Pyranose Ringmentioning

confidence: 99%

Configuration of the pyranoses in relation to their properties and nomenclature

Isbell¹

1937

J. RES. NATL. BUR. STAN.

View full text Add to dashboard Cite

show abstract

“…241 If methanol is added to the 2,2-dimethoxypropane reaction, then isopropylidene glycosides may be formed directly from the free sugar. If concentrated suifuric acid was employed as the catalyst, in the above reaction, then thermodynamic control operated and the 2,3-monoketal 340 was the major product.…”

Section: Copeland Andmentioning

confidence: 99%

Carbohydrate cyclic acetal formation and migration

Clode¹

1979

Chem. Rev.

250

View full text Add to dashboard Cite

“…The resin separated was eluted with 80 ml of 1 N HCI to afford 270 mg of a solid which showed a main spot at RfO. 16 on TLC using a solvent mixture of chloroform-acetone (2: 1 in volume). A solution of this solid in 4 ml of 2 N NaOH was heated under refluxing for 18 hr.…”

Section: Isolation Of N-acetyl-n-methyl-tetra-o-methyl-4-epidesfomic mentioning

confidence: 99%