93845-71-7

Upstream product

• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 98-88-4 benzoyl chloride 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 91738-34-0 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 

Downstream Products

• 1448356-77-1 C₃₁H₃₉F₃O₁₁SSi 

Relevant academic research and scientific papers

Synthesis of branched iminosugars through a hypervalent iodine(III)-mediated radical-polar crossover reaction

The synthesis of a novel type of branched iminosugars is described. This synthetic strategy is based on two key reactions: first, an aldol reaction with formaldehyde in order to introduce selectively the hydroxymethyl branch, and second, a tandem β-fragmentation-intramolecular cyclization reaction. The combination of both reactions afforded a battery of compounds exhibiting a great structural complexity, with the concomitant formation of a quaternary center, starting from readily available aldoses. With this approach we have demonstrated the usefulness of the fragmentation of anomeric alkoxyl radicals (ARF) promoted by the PhIO/I2 system for the preparation of new compounds with potential interest for both medicinal and synthetic chemists.

Synthesis of 3-C-(hydroxymethyl)erythritol and 3-C-methylerythritol.

3-C-(Hydroxymethyl)erythritol was prepared from 3-C-(hydroxymethyl)-2,3-O-isopropylidene-D-erythro-tetrofuranose (4) by hydrolysis followed by reduction, or by reduction followed by hydrolysis. Monotosylation of 4, followed by reduction with lithium aluminum hydride and hydrolysis, afforded 3-C-methylerythritol.