30645-02-4

Usage

Molecular Structure

A derivative of L-sorbopyranose with five trimethylsilyl groups attached to the hydroxyl groups.

Reactivity

Highly reactive due to the presence of trimethylsilyl groups, making it useful in protecting hydroxyl groups during chemical reactions.

Application in Organic Synthesis

Commonly used in the protection and deprotection of hydroxyl groups, as well as in the synthesis of complex organic molecules.

Utility in Pharmaceutical Research

Valuable tool for chemists and researchers working in the field of organic chemistry, particularly in the development of new pharmaceutical compounds.

Protection of Hydroxyl Groups

The trimethylsilyl groups attached to the hydroxyl groups protect them from unwanted side reactions, allowing for more controlled and selective synthesis of target molecules.

Upstream product

• 6347-01-9 fructopyranose 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 57-48-7 D-Fructose 
• 75-77-4 chloro-trimethyl-silane 

Relevant academic research and scientific papers

Catalytic activation of carbohydrates as formaldehyde equivalents for stetter reaction with enones

We disclose the first catalytic activation of carbohydrates as formaldehyde equivalents to generate acyl anions as one-carbon nucleophilic units for a Stetter reaction. The activation involves N-heterocyclic carbene (NHC)-catalyzed C-C bond cleavage of carbohydrates via a retro-benzoin-type process to generate the acyl anion intermediates. This Stetter reaction constitutes the first success in generating formal formaldehyde-derived acyl anions as one-carbon nucleophiles for non-self-benzoin processes. The renewable nature of carbohydrates, accessible from biomass, further highlights the practical potential of this fundamentally interesting catalytic activation.

Highly atom economical uncatalysed and I2-catalysed silylation of phenols, alcohols and carbohydrates, using HMDS under solvent-free reaction conditions (SFRC)

An uncatalysed silylation of phenols, regardless on the aggregate state and nature of the substituents with 0.55 equiv of HMDS under solvent-free reaction conditions (SFRC) at room temperature is reported. Sterically hindered phenols, carbohydrates and most of the alcohols additionally required a catalytic amount (up to 2 mol %) of iodine. The reaction protocol is very simple; obtaining a pure product, particularly of uncatalysed reactions, was frequently a completely solvent-free process.