357399-53-2

Upstream product

• 282526-14-1 methyl 2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-1-thio-β-D-glucopyranoside 
• 282525-99-9 methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-1-thio-β-D-glucopyranoside 
• 124-63-0 methanesulfonyl chloride 
• 357399-52-1 methyl 3-O-benzoyl-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylamino)-2-deoxy-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Conversion of glucosamine to galactosamine and allosamine derivatives: Control of inversions of stereochemistry at C-3 and C-4

The reactions of sodium benzoate with a series of trimesylates derived from glucosamine have been examined in an attempt to gain facile access to galactosamine analogues. Trimesylate 17, in which the amino group was protected as a phthalimide, underwent double displacement at positions 4 and 6 to give the dibenzoate 18 with the desired galactosamine configuration. In contrast, trimesylates 21 and 27, in which the amino groups were protected as acetamides, unexpectedly underwent double displacement at positions 3 and 6, giving products 22 and 28, respectively, with allosamine configurations.