Sugars thio, synthesis

Thio Sugars. III. Synthesis and Rearrangement of 2-(3,4,6-Tri-0-acetyl-2-amino-2-deoxy-/3-D-galactopyranosyl)-2-thiopseudourea Dihydrobromide and Analogs, M. L. Wolfrom, W. A. Cramp, and D. Horton,/. Org. Chem., 29, 2302-2305 (1964). 

W. Meyer zu Reckendorf and W. A. Boimer, Sulfur substitution products of amino sugars. VI. Synthesis of 2-amino-2-deoxy-3-thio-D-allose derivatives through thiazoline intermediates. Tetrahedron, 19 (1963) 1721-1725. 

A Michael addition-Nef reaction sequence was used in a synthesis of disaccharides. Addition of the sodium salt of 1-thio-D-glucose to sugar nitroolefin 112 gave a mixture of isomers 113. The subsequent deacetylation, followed by a Nef reaction, afforded the S -disaccharides 114 and 115 (Scheme 35).82... 

Studies have also been conducted on compounds containing a thio-carbonyl group. Photolysis of dimethylthiocarbamates produces128,129 mixtures of deoxy sugars and alcohols (see Table XVI). As the alcohols can be reconverted into dimethylthiocarbamates, and these re-irradiated, the synthesis and irradiation of these compounds offers a useful pathway to deoxy sugars. A simple mechanism for this reaction, based on the two possible a-cleavages resulting from thiocarbonyl excitation, is shown in Scheme 23. In addition, the possibility has been... 

D. Horton, Thio sugars Stereochemical questions and synthesis of antimetabolites, Pun AppL Chan. 42 301 (1973). 

H. Yuasa, O. Hindsgaul, and M. M. Palcic, Chemical-enzymatic synthesis of 5 -thio-lV-acetyllactosamine The first disaccharide with sulfur in the ring of the nonreducing sugar, J. Am. Chem. Soc. 114 5891 (1992). 

This article collates information on the reactivity of sugar isothiocyanates and isomeric thiocyanates, and illustrates some of the chemical properties that have contributed to the synthesis of nucleoside analogs,1719 and thio and deoxy sugars. 

In an article that collates information not extensively treated before, Z. J. Witczak (West Lafayette) describes the synthesis, chemistry, and preparative applications of monosaccharide thiocyanates and isothiocyanates the thiocyanate anion is an ambident nucleophile of great synthetic versatility in approaches to nucleoside analogs and to thio and deoxy sugars. 

Epoxy sugars are frequently used as starting compounds in the synthesis of sugar derivatives (compare Section IV) such as halo, amino, azido, thio, deoxy, and branched-chain derivatives. The oxirane ring is in general more reactive than the oxetane or oxolane ring. It is opened with nucleophiles under base or acid catalysis. On the other hand, the oxirane ring remains unattacked under the conditions of catalytic debenzylation on palladium,... 

Yuasa H, Hindsgaul O, Palcic MM (2002) Chemical-enzymic synthesis of 5 -thio-N-acetyllactosamine the first disaccharide with sulfur in the ring of the non-reducing sugar. J Am Chem Soc 114 5891-5892... 

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