83657-33-4

Upstream product

• 56119-05-2 4,6-O-isopropylidene-D-glucose 
• 50-70-4 D-sorbitol 
• 77-76-9 2,2-dimethoxy-propane 
• 53691-70-6 4,6-O-isopropylidene-D-glucopyranose 

Downstream Products

• 302579-03-9 (4S,5R)-5-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxane 

Relevant academic research and scientific papers

Synthesis of salacinol

Salacinol, a new type of α-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sul

The Biosynthesis of Thiamine. Syntheses of -1-Deoxy-D-threo-2-pentulose and Incorporation of this Sugar in Biosynthesis of Thiazole by Escherichia coli Cells

Non-growing, washed cells of Escherichia coli, depressed for the synthesis of thiamine, were incubated in the presence of -1-deoxy-D-threo-2-pentulose (9) in a medium containing the pyrimidine moiety of thiamine, L-tyrosine, and glucose.The thiamine thus biosynthesized was extracted and cleaved to give 5-(2-hydroxyethyl)-4-methylthiazole (HET) which was examined as the trifluoroacetate derived by electron-impact mass spectrometry.The distribution of the label in the fragments indicated that the pentulose (9) was a precursor of the C5-chain of HET without C-C bond cleavage.Several routes to 1-deoxypentuloses are described.Condensation of 2,4-O-benzylidene-D-threose (23) with trideuteriomethylmagnesium iodide gave the protected 1-deoxypentitols (24) and (25).Brominolysis of the mixed dibutylstannylidenes then afforded -3,4-O-benzylidene-1-deoxy-D-threo-2-pentulose (26), which was converted into the free sugar (9) by acidic hydrolysis. 1-Deoxy-D-erythro-2-pentulose was prepared in similar manner.Condensation of 2-(-methyl)-1,3-dithian with 2,3-O-isopropylidene-D-glyceraldehyde, followed by a C-3 epimerization step also led, after deprotection, to a mixture of -1-deoxy-D-erythro- and -1-deoxy-D-threo-2-pentulose, (5) and (6).