Condensation of D-mannosaldehyde derivatives with ethyl diazoacetate. An easy and stereoselective chain elongation methodology for carbohydrates: Application to new syntheses for KDO and 2-deoxy-β-KDO
作者： Fidel J López-Herrera , Francisco Sarabia-García
DOI: 10.1016/S0040-4020(97)00056-2
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摘要: R and 3S) ~-Hych'oxy-0t-diazocarbouyl compounds 4 (100%, 3:2), 9 (35%, 100:0), 14 (74%, 7:2) 18 (100%. 100:0). prepared from 2,3,4,5.6-penta-O-acetyl- (3), penta-O-benzyl- (8). 2.3:5,6-di-O-isopropylidene-4-O- (tert-butyldimethylsilyl)- (13), 2,3:5.6-di-O-isopropylidene-4-O-acetyl-D-mannosaldehyde (17), respectively, were acetylaled, the resulting (~-acetoxy-cc-diazocarbonyl treated with rhodium diacetate to give correspond- ing ¢~-enol esters. 6 (100%). 11 (35 %), 16 (100%) 20 which are potentially o~-keto Molecular mechanics calculations used in order justify stereoselectivity observed initial addition process. The problematic removal of protecting groups c~-enol esters is disccussed. Finally, hyda'azinolysis {~-enol acetates (to quench labile ~-keto ester as correspooding less reactive hydraziues), mild oxidation corresponding ct-diazoesters, deprotection, final oxidatiotl diazo group wit h m-chloroperbenzoic gave KDO good yield, lnterlnediate products completely stereoselective synthesis 2-deoxy-13-KDO, a potent inhibitor for CMP-KDO synthetase. © 1997 Published by Elsevier Science Ltd. All rights rescrved.
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