Erythritol: A Versatile Precursor for C‐4 Chiral Building Blocks

Abstract

Starting from erythritol, enzyme catalyzed construction of C4 chiral building blocks is described. The four diastereomeric protected tetroses are available from this single compound. Also an approach to L-and D-hexosederivatives is presented.

Diastereoselective Passerini Reaction of Biobased Chiral Aldehydes: Divergent Synthesis of Various Polyfunctionalized Heterocycles

“…It is biotechnologically produced from common sugars using various microorganisms and, thus, is a renewable feedstock. As previously reported by us and others, desymmetrization of its 2,3-acetonide using lipases can afford both monoester 1 and its pseudoenantiomer 2 in high ee. We reasoned that oxidation of 1 or 2 to the corresponding aldehydes (e.g., 3 ), followed by Passerini reaction, would afford interesting polyfunctionalized intermediates that could be manipulated to give a variety of heterocycles.…”

Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction

“…The Celite was washed several times with boiling THF and the filtrate was concentrated. The residue was triturated with Et 2 O to afford 11 (3.082 g, 82% yield) as a white solid, which analytical data are agree with the reported ones [21].…”

“…((4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanol ( 11 ). Method A: from erythritol through a known procedure [ 21 ]. Method B: D-isoascorbic acid 9 was transformed into lactone 10 , as previously reported [ 22 ].…”

“…Chiral building block 2 (Scheme 1) can be prepared by the chemoenzymatic desymmetrization of diol 11, which, in turn, was prepared from erythritol 1, as previously described (Scheme 2) [5,21]. However, we also developed an efficient alternative synthesis starting from D-isoascorbic acid 9, an antioxidant readily accessible from simple sugars.…”

Verfahrensentwicklung zur mikrobiellen Herstellung von Erythrit

“…Erythrit besitzt eine Vielzahl an Anwendungsfeldern in denen es direkt oder als Derivat angewendet werden kann und stellt somit einen wichtigen Building-block für die chemische und pharmazeutische Industrie dar [71]. Die Verwendung von Erythrit in der pharmazeutischen Technik zum Überziehen von Medikamenten durch Sprühcoating verspricht viele Vorteile, da Erythrit nicht mit anderen Inhaltsstoffen Wechselwirkungen zeigt und sich durch seine physikochemischen Eigenschaften wie hohe Wasserlöslichkeit, niedrige Hygroskopizität, spontane Kristallisation und niedrige Klebkraft [72] auszeichnet.…”