847673-10-3

Upstream product

• 108-24-7 acetic anhydride 
• 847555-66-2 D-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro-3-O-methyl-5,6-O-[(R/S)-2,2,2-trichloroethylidene]-chiro-inositol 

Relevant academic research and scientific papers

Concentrated hydriodic acid in simultaneous deprotections of multifunctional inositols

L-1-Deoxy-1-fluoro-6-O-methyl-myo-inositol was epimerized by chloral/DCC in boiling 1,2-dichloroethane yielding d-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro- 3-O-methyl-5,6-O-[(R/S)-2,2,2-trichloroethylidene]-chiro-inositol. The latter and l-4-O-benzyl-3-O-cyclohexylcarbamoyl-5-O-methyl-1,2-O-(2,2,2- trichloroethylidene)-muco-inositol, l-4-O-benzyl-3-O-cyclohexylcarbamoyl-1,2-O- ethylidene-5-O-methyl-muco-inositol, d-1-O-cyclohexylcarbamoyl-2-deoxy-5,6-O- ethylidene-2-fluoro-3-O-methyl-chiro-inositol, as well as d-5-O-benzyl-4-O- cyclohexylcarbamoyl-3-deoxy-3-(N,N′-dicyclohexylureido)-6-O-methyl-1, 2-O-(2,2,2-trichloroethylidene)-chiro-inositol were deprotected with boiling 57% aq hydrogen iodide. Ether, urethane and ethylidene acetal functions were simultaneously cleaved by the reagent, whereas the trichloroethylidene groups were still intact or were only removed in small quantities. Especially, the urea function of d-5-O-benzyl-4-O-cyclohexylcarbamoyl-3-deoxy-3-(N,N′- dicyclohexylureido)-6-O-methyl-1,2-O-(2,2,2-trichloroethylidene)-chiro-inositol was decomposed to a cyclohexylamino group. The hydrodechlorination of d-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro-3-O-methyl-5,6-O-[(R/S)-2,2, 2-trichloroethylidene]-chiro-inositol using Raney-Nickel yielded a mixture of the corresponding 5,6-O-ethylidene- and 5,6-O-chloroethylidene derivatives. The three synthetic steps-hydrodehalogenation, HI-deprotection and peracylation- were combined without purification of the intermediates.

D-2-Deoxy-2-fluoro-chiro-inositol-a new member of the deoxy fluoro inositol family

An efficient synthetic route to D-2-deoxy-2-fluoro-chiro-inositol has been developed with inversions of the C-1 and C-5 configuration of L-quebrachitol. The key steps of the route are two consecutive one pot epimerization procedures which do not require t