Related Experiment Video
Updated: Jul 16, 2026

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
Efficient synthesis of methylene exo-glycals: another use of glycosylthiomethyl chlorides
Xiangming Zhu1, Ying Jin, John Wickham
1Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland. xiangming.zhu@ucd.ie
Abstract:
A new approach to the synthesis of methylene exo-glycals is described. Oxidation of glycosylthiolmethyl chloride (GTM-Cl) with mCPBA afforded the corresponding glycosylchloromethyl sulfone in almost quantitative yield, which underwent KOtBu-induced Ramberg-Bäcklund rearrangement to furnish the desired methylene exo-glycal in excellent yield.
Related Concept Videos
Preparation and Reactions of Sulfides
Multiple Halogenation of Methyl Ketones: Haloform Reaction
Preparation and Reactions of Thiols
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane

