15667-21-7Relevant articles and documents
Enzyme-catalyzed asymmetric synthesis; 10. Pseudomonas cepacia lipase mediated synthesis of enantiomerically pure (2R,3S)- and (2S,3R)-2,3-O-cyclohexylideneerythritol monoacetate from 2,3-O-cyclohexylideneerythritol
Gais,Hemmerle,Kossek
, p. 169 - 173 (1992)
Pseudomonas cepacia lipase catalyzed hydrolysis of 2,3-O-cyclohexylideneerythritol diacetate in an emulsion of water and diisopropyl ether gives (2S,3R)-2,3-O-cyclohexylideneerythritol monoacetate [(2S,3R)-1-acetoxy-2,3-cyclohexylidenedioxy-4-hydroxybutane] with ≥ 99% ee in 91% yield by a preferential attack at the R-center CH2OAc group. The enantiomeric (2R,3S)-2,3-O-cyclohexylideneerythritol monoacetate is obtained by acetylation of 2,3-O-cyclohexylideneerythritol with vinyl acetate catalyzed by the same enzyme with ≥ 99% ee in 78% yield by a combined enantiotopos and enantiomer differentiation through a preferential attack at the R-center CH2OH groups.
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Giudici,Fluharty
, p. 2043 (1967)
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General Synthetic Approach to Rotenoids via Stereospecific, Group-Selective 1,2-Rearrangement and Dual S N Ar Cyclizations of Aryl Fluorides
Matsuoka, Seiya,Nakamura, Kayo,Ohmori, Ken,Suzuki, Keisuke
, p. 1139 - 1156 (2019/02/26)
A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) S N Ar oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to (-)-rotenone and (-)-deguelin, was prepared from d -araboascorbic acid in five steps. Also described is the conversion of (-)-deguelin into oxidized congeners, (-)-tephrosin and (+)-12a- epi -tephrosin.
A method for synthesizing tetranoic acid
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Paragraph 0029-0040, (2017/03/08)
The invention discloses a synthetic method of tetronic acid. The synthetic method comprises the following steps: firstly oxidizing low-price easily-available natural sodium D-isoascorbate as a raw material through hydrogen peroxide, and acidifying through hydrochloric acid to prepare a key synthetic intermediate, namely erythronolactone; secondly, reacting erythronolactone with sulfonyl chloride to generate crude tetronic acid; finally, simply re-crystallizing obtained crude tetronic acid to obtain pure tetronic acid. The synthetic method has the characteristics of few synthetic steps, simple and convenient process, low synthetic cost, convenience for large-scale industrialized production and the like; finally obtained pure tetronic acid is high in yield and purity, the yield can reach more than 87%, and the purity can reach more than 99%.