211623-14-2Relevant academic research and scientific papers
A preparation of protected 2-deoxy-2-hydroxymethyl-D-mannose and -D- glucose derivatives not involving organometallic reagents
Malleron, Annie,David, Serge
, p. 93 - 98 (1998)
The branched chain protected sugar, 2-C-hydroxymethyl-2,3;5,6-di-O- isopropylidene-D-mannofuranose was specifically benzylated at the primary hydroxyl group position by the stannylene procedure (93%). Oxidation with pyridinium chlorochromate gave in 71% yield 2-C-benzyloxymethyl-2,3;5,6-di- O-isopropylidene-D-mannonolactone which was reduced with 3 equiv of samarium diiodide in oxolane to a 56:44 mixture of the 2-deoxy derivatives, 2-C- benzyloxymethyl-2-deoxy-5,6-O-isopropylidene-D-mannono- (5) and -D-glucono- lactones in 83% combined yield. Reduction of lactone 5 with DIBAH in dichloromethane gave the protected branched chain sugar, 2-C-benzyloxy-2- deoxy-5,6-O-isopropylidene-D-mannose in 63% yield. In the reduction of 2-C- hydroxymethyl-2,3;5,6-di-O-isopropylidene-D-mannonolactone and 2-C- hydroxymethyl-D-mannonolactone in water solution, only lactones with the D- manno configuration, 2-deoxy-2-C-hydroxymethyl-5,6-O-isopropylidene-D- mannonolactone and 2-deoxy-2-C-hydroxymethyl-D-mannono-(1,5)-lactone, could be isolated or characterized among the products of the reaction.
