Publisher Summary This chapter discusses sucrose chemistry and the applications of sucrochemicals. The use of sucrose as a chemical raw material was first motivated by the desire to increase the small proportion of the total production dedicated to the applications of higher value, essentially for nonfood uses. The conformational structure of sucrose is essentially based on the intramolecular hydrogen-bond network that connects hydroxyl groups from the glucose and the fructose moieties. Some scales of relative acidity of the hydroxyl groups of sucrose, converging on the highest acidity for OH-2, can be established either by semi-empirical calculations or be deduced from the distribution of the regio-isomers after selective substitution. It is found that because of the high stability of the ether function, etherification of unprotected sucrose leads to a kinetic distribution of products directly reflecting the relative reactivity of the hydroxyl groups. Specific microorganisms, yeasts, and bacteria can also convert sucrose into other alcohols, as well as organic acids, amino acids, and vitamins. All these biological processes have been improved with the help of modern biotechnology, making them more chemically and economically efficient and to direct them toward new and useful chemical products.

Sucrose chemistry and applications of sucrochemicals.

Discussed herein is the synthesis of partially protected carbohydrates by manipulating only one type of a protecting group for a given substrate. The first focus of this review is the uniform protection of an unprotected starting material in a way that only one (or two) hydroxyl group remains unprotected. The second focus involves regioselective partial deprotection of uniformly protected compounds in a way that only one (or two) hydroxyl group becomes liberated.

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Synthesis of carbohydrate building blocks via regioselective uniform protection/deprotection strategies

Carbohydrates from Detarium microcarpum bark extract.

Synthesis of sucrose epoxides, partial de-esterification of 1′,2:4,6-di-O-isopropylidenesucrose tetra-acetate, and selective tosylation of 3,6′-di-O-acetyl-1′,2:4,6-di-O-isopropylidenesucrose☆

Regioselective enzymic deacetylation of octa-O-acetyl-sucrose: preparation of hepta-O-acetylsucroses

Selective deacetylation of sucrose octa-acetate with primary amines to give 2,3,4,6,1′,6′-hexa-O-acetylsucrose

Synthesis and reactions of cyclic acetal derivatives of 6,6′-dichloro-6,6′-dideoxysucrose☆

Sucrose octabenzoate: assignment of 13C and 1H resonances of the sucrose moiety and the 13C resonances of the carbonyl carbons. Use of 13C-n.m.r. spectroscopy for the study of selective deacylation.

A male fertility-inhibiting composition in unit dosage form, contains as an active ingredient a 6-chlorodeoxy-saccharide containing a pyranose or furanose ring of the formula ##STR1## where A represents the remainder of the pyranose or furanose ring, and has the formula C 4 H 7 O 4 X (where X represents a hydrogen atom or another pyranose or furanose ring) in association with a physiologically acceptable carrier or excipient. The saccharide preferably contains a pyranose ring or furanose ring of the formula ##STR2## Also a method of controlling fertility in men or male animals comprises administering thereto a 6-chlorodeoxy-saccharide as defined above.

Haydn F. Jones

Papers

Selective deacetylation of sucrose octa-acetate with primary amines to give 2,3,4,6,1′,6′-hexa-O-acetylsucrose

Synthesis and reactions of cyclic acetal derivatives of 6,6′-dichloro-6,6′-dideoxysucrose☆

Sucrose octabenzoate: assignment of 13C and 1H resonances of the sucrose moiety and the 13C resonances of the carbonyl carbons. Use of 13C-n.m.r. spectroscopy for the study of selective deacylation.

Male fertility-inhibiting compositions of 6-chlorodeoxy-saccharides