19200-26-1

Upstream product

• 2280-44-6 D-Glucose 
• 128-04-1 sodium dimethyldithiocarbamate 

Downstream Products

• 106756-74-5 (2R,3R,4R,5S,6R)-2-allyl-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 154-58-5 1,5-anhydro-D-glucitol 
• 96689-92-8 α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose 
• 19200-24-9 2,3,4,6-tetra-O-acetyl N,N-dimethyl S-β-glucopyranosyl dithiocarbamate 

Relevant academic research and scientific papers

Protection-free synthesis of glycosyl dithiocarbamates in aqueous media by using 2-chloroimidazolinium reagent

Glycosyl dithiocarbamates (GDTCs) have been synthesized directly from the corresponding unprotected sugars and dithiocarbamate salts in good yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as condensing agent in aqueous media. The three-component one-pot synthesis of GDTCs starting from unprotected sugars, carbon disulfide, and secondary amines has also been successfully demonstrated. This is the first report on the direct synthesis of GDTCs from unprotected sugars without using any protecting groups.

Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates

2-Chloro-1,3-dimethylimidazolinium chloride (DMC, herein also referred to as Shoda's reagent) and its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations. This mini-review summarizes the development of DMC and some of its derivatives/analogues, and highlights recent applications for protecting group-free synthesis.

First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates

A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H3PO2-NaHCO3 system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.