Chain Elongation of Aldonolactones
- 1 January 1990
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 9 (6) , 809-822
- https://doi.org/10.1080/07328309008543876
Abstract
As an alternative to the classical Reformatsky-type branching reaction of aldonolactones, ethyl trimethylsilylacetate, methyl 2-trimethylsilyl-propionate, trimethylsilylacetonitrile or alkyl 2-(trimethylsilylmethyl)-acrylates in the presence of catalytic amounts of tetra-n-butyl-ammonium fluoride can be used. The corresponding chain elongated monosaccharides are obtained in high yields.This publication has 18 references indexed in Scilit:
- Fluoride-ion mediated reaction between trimethylsilylacetonitrile and carbonyl compounds. A new synthesis of β-trimethylsilyloxy nitritesJournal of the Chemical Society, Perkin Transactions 1, 1989
- One-Pot Synthesis of α-Mono- and α,α-Disubstituted Cyclic Ethers from LactonesChemistry Letters, 1988
- Radical Anomefhc ChemistryJournal of Carbohydrate Chemistry, 1988
- Synthesis of Carbohydrate Derived α-Methylene-γ-lactones by Diasterecseldctive, Low Temperature Reformatsky-Type ReactionsJournal of Carbohydrate Chemistry, 1986
- Deoxy‐nitrosugars 15th communication Synthesis of N‐acetylneuraminic acid and N‐acetyl‐4‐epineuraminic AcidHelvetica Chimica Acta, 1986
- Branching of Ketosugars by Ethyl Trimethylsilyl-Acetate/Tetra-n-Butylammonium FluorideJournal of Carbohydrate Chemistry, 1986
- An organotransition metal based approach to the synthesis of C-glycosidesJournal of the American Chemical Society, 1985
- C-Glycosidation of pyridyl thioglycosidesJournal of the American Chemical Society, 1985
- Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular modelJournal of the American Chemical Society, 1985
- A Simple Synthesis of (2-Ethoxycarbonylallyl)-trimethylsilane, A Potential Synthon for the Synthesis of 2-Methylene-4-alkanolidesSynthesis, 1985