Carbohydrate Research p. 107 - 115 (1995)
Update date:2022-08-05
Topics:
Limberg
Thiem
The well-known β-elimination of protected aldonolactones is used for the synthesis of the short-chain 2-keto-3-deoxyaldonic acids 1-4 containing four to six carbon atoms. The key step is the facile β-elimination step which generates the desired 2-keto-3-deoxy acids as protected enol 1,4-lactones in excellent yields. Smooth deprotection then leads to the 2-keto-3-deoxyaldonic acids. In the case of the protected D-galactono-1,4-lactone 6 an epimerisation is observed during the elimination process. This enables the synthesis of both 2-keto-3-deoxy-D-hexonic acids with either D-erythro (1) or D-threo (2) configuration in good to excellent yields in only three steps starting with commercially available D-galactono-1,4-lactone (5).
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Doi:10.1016/j.cclet.2013.11.004
(2014)Doi:10.1080/00397911.2020.1825742
(2021)Doi:10.1002/recl.19951140905
(1995)Doi:10.1002/adsc.200390003
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(1995)Doi:10.1021/jm020940p
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