Concise synthesis of 3-deoxy-d-manno-oct-2-ulosonic acid (KDO) as a protected form based on a new transformation of α,β-unsaturated ester to α-oxocarboxylic acid ester via diol cyclic sulfite
作者： Atsuhito Kuboki , Toshihiro Tajimi , Yoshihide Tokuda , Dai-ichiro Kato , Takeshi Sugai
DOI: 10.1016/J.TETLET.2004.04.016
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摘要: Abstract A concise synthesis of KDO ( 1 ) as the suitably protected form 2 from 2,3:5,6-di- O -isopropylidene-α- d -mannofuranose 3 was achieved in five steps (overall 65% yield). The key step is efficient transformation readily available α,β-unsaturated ester to α-oxocarboxylic acid ester. newly β-elimination corresponding diol cyclic sulfite and situ trap (DBU/TMSCl) into enol silyl ether developed give tautomeric equivalent deprotection labile TMS provided desired product.
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