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β-Oxy-α-diazo-carbonyl compounds. Part 6: Synthesis and reactivity of 3-deoxy-2-diazo-esters derived from monosaccharides. Applications in the synthesis of 2-C-alkyl-KDO analogues and related compounds

✍ Scribed by Francisco Sarabia; Fidel Jorge López-Herrera

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
91 KB
Volume
42
Category
Article
ISSN
0040-4039

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Reactions of ethyl 2-diazoacetate with aldehydo sugars and monosaccharide derivatives in their hemiacetal form are reported. The use of diethyl zinc led to an improvement of yields and shorter reaction times compared with neutral conditions as previously described. The resulting products represent p

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p-Acemxy-a4iaz.o esters yield a-en01 amate esters quantitatively by reaction with dirhodittm temmtate. The reaction was used to prepare tJte major natural cmtpounds 3-Deoxy-D-arabiio-2-Heptulosonic lrcid (DAH, 1) aud 3-Deoxy-D-manno-2-Cktulo.wnic