Sugars 4-deoxy-, synthesis

Rupprath, C., Kopp, M., Hirtz, D. et al. (2007) An enzyme module system for in situ regeneration of deoxythymidine 5 -diphosphate (dTDP)-activated deoxy sugars. Advanced Synthesis Catalysis, 349, 1489-1496. 

I. I. Cubero and M. T. P. Lopez-Espinosa, Branched-chain sugars. 12. Synthesis of 3,4-anhydro-l-deoxy-3-C-methyl-D-hexulose derivatives, Carbohydr. Res., 154 (1986) 71-80. 

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. 

Bellosta V, Czemecki S (1993) C-glycosyl compounds. Part X. Reaction of organocuprate reagents with protected 1,2-anhydro sugars. Stereocontrolled synthesis of 2-deoxy-C-glycopsyl compounds. Carbohydr Res 244 275-284... 

An alternative approach to the use of a-aminoketones involves acetals (72JOC221) and pyrazine-2,3-diones have been synthesized by this route (Scheme 58). The acetals are readily available from the phthalimido derivatives via the a-chloroketones. Hemiacetals have also served as a starting point for pyrazine synthesis, although in most cases hemiacetals are too labile to be easily prepared examples are common in the 2-amino-2-deoxy sugar series 2-amino-2-deoxy-D-glucose for example dimerizes to the pyrazine (101) when generated in situ from the hydrochloride salt (68JAP6813469). 

Vasella has used deoxy-nitro sugars for the synthesis of various biologically important carbohydrates, and the radical nitromethyladon of deoxy-nitro sugars has been used for synthesis of fnictose 6-phosphate" and 6-C-methyl and 6-C-rhydroxymethyl analogiies of iV-acetylnenraitinic acid fsee Scheme7.2. ... 

A presentation by Webber and co-workers dealing with the synthesis of fluorodeoxy sugars regrettably had to be left out of this monograph because of unexpected difficulties in the preparation of the manuscript. The fourth aspect was represented in the symposium by two presentations involving important aspects of deoxy and dideoxy sugars by Osborn and Heath respectively which unfortunately were not incorporated in this monograph. 

The deoxyinositols (quercitols, cyclohexanepentols) are useful model compounds which display many of the physical and chemical properties of true deoxy sugars. Although (-b)-proto-quercitol, the best known isomer, was isolated from nature 118 years ago, no synthesis has been reported up until now. The synthesis here described is actually that of the (-)-enantiomer, starting with (-)-inositol however, identical procedures applied to the readily available ( + ) or dl-inositol would give (- -) or DL-proto-quercitol, respectively. The natural occurence of, )-proto-quercitol has... 

Synthesis of Ring-Deoxy Sugars (Pseudo-Hexoses)... 

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