Chain Elongation of Sugars with Ethyl Isocyanoacetate
Abstract
Addition of Ethyl Isocyanoacetate to 3-O-Benzyl-1,2-O-Isopropylidene-Α-D-Ribo-Pentodialdo-1,4-Furanose in Ethanolic Sodium Cyanide Gave Two Oxazolines that Were Hydrolysed during Chromatography to Two Isomeric Ethyl 3-O-Benzyl-6-Deoxy-6-Formamido-1,2-O-Isopropylidene-Heptofuranuronates. Similarly, 1,2-O-Isopropyl-Idene-3-O-Methyl-Α-D-Xylo-Pentodialdo-1,4-Furanose Gave the 3-O-Methyl-Heptofuranuronates 7 and 11. Reduction of 7 and 11 Gave N-Methylamino Esters that Exhibited Cotton Effects from Which the Configurations at C-6 of 7 and 11 Were Deduced. the Chiralities at C-5 of 7 and 11 Were Established by Tetrahydropyranlation of 7 and 11, Followed by Consecutive Treatment with Bis(2-Methoxyethoxy)aluminium Hydride, Periodate, Sodium Borohydride, and Dilute Acid, to Give 1,2-O-Isopropylidene-3-O-Methyl-Α-D-Glucofuranose and its Β-L-Ido Epimer, Respectively. Attempts to Methylate HO-5 of 7 and 11 Resulted in Elimination. on Formylaminomethylenation (Ethyl Isocyanoacetate and Potassium Hydride in Tetrahydrofuran), 3-O-Benzyl-1,2-O-Isopropylidene-Α-D-Ribo-Pentodialdo-1,4-Furanose and its 3-O-Methyl-Α-D-Xylo Epimer Each Gave (E)- and (Z)-Mixtures of Alkenes that Were Hydrogenated to Give Mixtures of 5,6-Dideoxy-6-Formamido-Heptofuranuronates. © 1978.
Recommended Citation
Bischofberger, K., Brink, A. J., De Villiers, O. G., Hall, R. H., & Jordaan, A. (1978). Chain Elongation of Sugars with Ethyl Isocyanoacetate. Carbohydrate Research, 64, pp. 33-42. Elsevier.
The definitive version is available at https://doi.org/10.1016/S0008-6215(00)83685-X
Department(s)
Business and Information Technology
International Standard Serial Number (ISSN)
0008-6215
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2023 Elsevier, All rights reserved.
Publication Date
01 Jan 1978
