99902-26-8Relevant articles and documents
A highly stereoselective synthesis of the 1β-methylcarbapenem key intermediate from (R)-3-hydroxybutyric acid
Kobayashi, Yuko,Ito, Yoshio,Terashima, Shiro
, p. 55 - 66 (2007/10/02)
(3R,4R)-4-Acetoxy-3-[(R)-1-(formyloxy)ethyl]-2-azetidinone 6 could be prepared highly stereoselectivity from (R)-3-hydroxybutyric acid by employing the [2+2]-cycloaddition reaction of chlorosulfonyl isocyanate with the 2H,4H-1,3-dioxin derivative and the Baeyer-Villiger reaction accompanying novel cleavage of the acetal moiety. The Reformatsky reaction of 6 with sterically crowded 3-(2-bromopropionyl)-2-oxazolidone derivatives readily afforded the title key intermediate after sequential chemical manipulations.
ELECTROPHILIC AMINATION: ENANTIOSELECTIVE SYNTHESES OF D-ALLOTHREONINE AND L-THREONINE
Genet, J. P.,Juge, S.,Mallart, S.
, p. 6765 - 6768 (2007/10/02)
Starting from inexpensive polyhydroxybutanoate (PHB), D-allothreonine 1 and L-threonine 2 were synthetized by a sequence involving a diastereoselective electrophilic amination.When (R) 3-hydroxybutanoic acid was protected as dioxanone 9 very good yield (>95percent) and high diastereomeric excess (>99percent) were obtained in the amination step.
Optisch aktive Alkohole aus 1,3-Dioxan-4-onen; eine praktikable Variante der asymmetrischen Synthese unter nucleophiler Substitution an Acetalzentren
Seebach, Dieter,Imwinkelried, Rene,Stucky, Gerhard
, p. 182 - 183 (2007/10/02)
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