PubMed · 7076913
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M K McCray, C Zugerman. 1982. 2-Deoxy-D-glucose for herpes simplex?. https://doi.org/10.1016/s0190-9622(82)80380-0
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A photoinduced electron-transfer (PET) reaction was used for the deoxygenation at C-2 of aldonolactones derivatized as 2-O-[3-(trifluoromethyl)benzoyl] or benzoyl esters. By irradiation of different D-galactono- and D-glucono-1,4-derivatives, with a 450W lamp, using 9-methylcarbazole as photosensitizer, the corresponding 2-deoxy-D-lyxo- and 2-deoxy-D-arabino-hexono-1,4-lactones were efficiently obtained.
Replacement of specific hydroxyl groups by fluorine in carbohydrates is an ongoing challenge from chemical, biological, and pharmaceutical points of view. A rapid and efficient two-step, regio- and stereoselective synthesis of 2-deoxy-2-(R)-fluoro-beta-d-allose (2-(R)-fluoro-2-deoxy-beta-d-allose; 2-FDbetaA), a fluorinated analogue of the rare sugar, d-allose, is described. TAG (3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-d-arabino-hex-1-enitol or 3,4,6-tri-O-acetyl-d-glucal), was fluorinated in anhydrous HF with dilute F(2) in a Ne/He mixture or with CH(3)COOF at -60 degrees C. The fluorinated intermediate was hydrolyzed in 1N HCl and the hydrolysis product was purified by liquid chromatography and characterized by 1D (1)H, (13)C, and (19)F NMR spectroscopy as well as 2D NMR spectroscopy and mass spectrometry. In addition, (18)F-labeled 2-deoxy-2-(R)-fluoro-beta-d-allose (2-[(18)F]FDbetaA) was synthesized for the first time, with an overall decay-corrected radiochemical yield of 33+/-3% with respect to [(18)F]F(2), the highest radiochemical yield achieved to date for electrophilic fluorination of TAG. The rapid and high radiochemical yield synthesis of 2-[(18)F]FDbetaA has potential as a probe for the bioactivity of d-allose.
[reaction: see text] A general procedure for the stereoselective synthesis of 2-deoxy-2-iodo-hexo- and -hepto-pyranosyl glycosides from furanoses is reported. The proposed methodology provides a new route for accessing 2-deoxy-oligosaccharides. The procedure involves three reactions: Wittig-Horner olefination to give alkenyl sulfanyl derivatives, electrophilic iodine-induced cyclization to give phenyl 2-deoxy-2-iodo-1-thio-hexo-glycosides, and glycosylation. Protected furanoses 1, 3, and 6-11, which include examples of the four possible isomeric configurations of furanoses, were reacted with diphenyl phenylsulfanylmethyl phosphine oxide to give the alkenyl sulfanyl derivatives 2, 4, and 12-16. The iodine-induced cyclization of these compounds afforded the phenyl 2-deoxy-2-iodo-1-thio-glycosides 18, 20, and 22-27 with practically complete regio- and stereoselectivity. Products of 6-endo cyclization, in which the iodine at C-2 was in a cis relationship with the alkoxy at C-3, were almost exclusively produced. Better yields were obtained for compounds with a ribo or xylo configuration than for compounds with other configurations. Compounds 18, 20, and 22-27 were found to be efficient glycosyl donors in the glycosylation of cholesterol and glucopyranoside 29a, affording the corresponding 2-deoxy-2-iodo-glycosides and 2-deoxy-2-iodo-oligosaccharides with good yields and stereoselectivities. The glycosydic bond in the major isomers was always trans to the iodine at C-2.