Syntheses of L-Threose and Methyl Di-O-acetyl-L-threuronate fromdextro-Tartaric Acid
| Autor: | Haruo Edo, Masazumi Nakagawa, Gen Nakaminami |
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| Rok vydání: | 1973 |
| Předmět: | |
| Zdroj: | Bulletin of the Chemical Society of Japan. 46:266-269 |
| ISSN: | 1348-0634 0009-2673 |
| DOI: | 10.1246/bcsj.46.266 |
| Popis: | Reduction of methyl hydrogen di-O-acetyl-dextro-tartrate (I) with sodium borohydride in water afforded L-threono-γ-lactone (II). L-Threose (IV) was obtained on treatment of the γ-lactone (II) with an excess of disiamylborane. Reduction of ester chloride of di-O-acetyl-dextro-tartaric acid (VI) with tri-n-butyltin hydride yielded methyl di-O-acetyl-L-threuronate (VII). Attempts to reduce 2-deoxy-pentarate ester (X) derived from ester chloride (VI) via diazoketone (VIII) with sodium borohydride to give 2-deoxy-threo-pentono-γ-lactone (XI) gave unsatisfactory results. Formation of methyl L-threo-2,3-di-O-acetyl-5-chloro-5-deoxy-4-C-hydroxymethyl-4,4′-anhydropentonate (IX) in addition to diazoketone (VIII) was observed when ester chloride (VI) was treated with an excess of diazomethane. On the basis of the observed (−)-Cotton effect in the 290 nm region of ORD and CD spectra of L-threose (IV) and D-erythrose, possibility of the presence of an open chain non-hydrated alde-hyde-form of aldotetrose in water was ... |
| Databáze: | OpenAIRE |
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