By David C. Baker, Derek Horton
Advances in Carbohydrate Chemistry and Biochemistry, a part of an extended working serial that begun in 1945, presents serious and informative articles written by way of learn experts that combine the commercial, analytical, and technological features of biochemistry, natural chemistry, and instrumentation technique within the examine of carbohydrates. every one article presents a definitive interpretation of the present prestige and destiny developments in carbohydrate chemistry and biochemistry.
- Features contributions from major experts and specialists who concentrate on carbohydrate chemistry, biochemistry, and research
- Integrates the commercial, analytical, and technological features of biochemistry, natural chemistry, and instrumentation method within the research of carbohydrates
- Informs and updates on the entire most recent advancements within the box
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Extra resources for Advances in Carbohydrate Chemistry and Biochemistry, Volume 72
5% D-gluco isomer. 93–95 Medakovic´96 and more recently Wong and coworkers97 reported that the ratio of L-ido to D-gluco products could be improved to 3:1 when the α-acetate 40b is used as the starting material and the reduction was carried out at lower temperature in refluxing benzene on the derived bromo compound 41b to give 42b. 98,99 Interestingly, when carried out in benzene at reflux the reaction led exclusively to the L-idopyranosyl fluoride 44 in Scheme 5 Synthesis of IdoA derivatives via radical reduction of C-5 bromo compounds.
36,37 Lactone 3a was treated with ethanethiol and concentrated hydrochloric acid resulting in simultaneous removal of the isopropylidene group and C-1 thioacetalization to give dithioacetal 4 in quantitative yield. This was followed by regioselective formation of the 2,4-O-p-methoxybenzylidene derivative 5 under standard conditions. The lactone ring of 5 was then opened with methylamine in THF to give the L-iduronamide in 91% yield. The formation of the amide was necessary to prevent reformation of the lactone ring, which occurred during attempts to convert 5 into the corresponding methyl ester by methanolysis.
Compound 149 was then subjected to epoxidation using in situ generated methyl(trifluoromethyl)dioxirane (TFDO) leading to a diastereomeric mixture (1:9) of L-gulo- and L-talo-epoxides 150 and 151 in a total yield of 79%. Finally, epoxide ring opening of L-talo-epoxide 151 under alkaline conditions afforded the L-idose derivative 152 in 99% yield. The regioselectivity of the epoxide ring opening was attributed to attack of the hydroxide ion from the relatively unhindered C-3 position of the 5Ho conformer of 151.
Advances in Carbohydrate Chemistry and Biochemistry, Volume 72 by David C. Baker, Derek Horton