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Generated: September 23, 2017

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Title:Synthesis of UDP-Glucose: N-acylsphingosine glucosyl transferase inhibitors
Abstract: Disclosed is a novel enantiomeric synthesis ceramide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.
Inventor(s): Hirth; Bradford H. (Littleton, MA), Siegel; Craig (Woburn, MA)
Assignee: Genzyme Corporation (Cambridge, MA)
Filing Date:Mar 14, 2012
Application Number:13/420,108
Claims:1. A method of preparing a sphingosine-like compound represented by the following structural formula: ##STR00032## said method comprising the stop of reacting a cyclic starting material with HNR.sub.2R.sub.3,said starting material represented by the following structural formula: ##STR00033## thereby forming an intermediate represented by the following structural formula: ##STR00034## and hydrolyzing the amino acetal group of the intermediate, thereby forming an acyclic compound represented by the following structural formula: ##STR00035## reacting the acyclic compound with an amide reducing agent, thereby forming an amine compound represented by the following structural formula: ##STR00036## debenzylating the --NHCH(--CH.sub.2OH)R.sub.5 group of the amine compound, thereby forming a sphingosine-like compound represented by the following structural formula: ##STR00037## wherein: R.sub.1 is a substituted or unsubstituted aromatic group; R.sub.2 and R.sub.3 are independently --H, a substituted or unsubstituted aliphatic group or, taken together with the nitrogen atom to which they art bonded, are a substituted or unsubstituted non-aromatic heterocyclie ring; and R.sub.5 is a substituted or unsubstituted aromatic group.

2. The method of claim 1 wherein the amine compound is debenzylated by hydrogenation.

3. The method of claim 2 wherein the amine compound is debenzylated by hydrogenation under a hydrogen atmosphere with a catalytic amount of a hydrogenation catalyst.
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