Syntheses of l-Threose and Methyl Di-O-acetyl-l-threuronate from dextro-Tartaric Acid
- 1 January 1973
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 46 (1) , 266-269
- https://doi.org/10.1246/bcsj.46.266
Abstract
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 discussed.This publication has 21 references indexed in Scilit:
- Total Syntheses of Carbohydrates, IV. 2-Deoxy-Dl-, l- and d-erythro-pentoses and Related SugarsBulletin of the Chemical Society of Japan, 1972
- 2-Amino-5,6-dihydro-1,3-oxazines. The Reduction of Carboxylic Esters with Sodium Borohydride1The Journal of Organic Chemistry, 1963
- Tetrose‐ und Pentosederivate aus (+)‐WeinsäureEuropean Journal of Inorganic Chemistry, 1961
- Synthese der L‐Apiose aus (+)‐WeinsäureEuropean Journal of Inorganic Chemistry, 1959
- Sodium Borohydride Reduction of Aldonic Lactones to Glycitols1Journal of the American Chemical Society, 1956
- Sodium Borohydride as a Reducing Agent in the Sugar Series1Journal of the American Chemical Society, 1952
- Sodium Borohydride as a Reducing Agent for Sugar Lactones1Journal of the American Chemical Society, 1951
- The Reduction of Tartaric Acid1Journal of the American Chemical Society, 1941
- The Chemistry of the Tetrose Sugars. II. The Degradation of d-Xylose by the Method of Wohl. The Rotation of d-Threose1Journal of the American Chemical Society, 1935
- The Chemistry of the Tetrose Sugars. I. A Crystalline Triacetate of d-Threose from the Degradation of Strontium Xylonate with Hydrogen Peroxide. Nomenclature in the Tetrose Group1Journal of the American Chemical Society, 1935