330808-18-9Relevant academic research and scientific papers
Total synthesis of a protected form of 2,6-anhydro-5-azido-3,5-dideoxy-2-C-hydroxymethyl-L-allo-heptose; a potential precursor of analogs of C-glycosides of neuraminic acid
Carrel, Frederic,Vogel, Pierre
, p. 4661 - 4680 (2000)
The title aldehyde (-)-3 and its enantiomer (+)-3 have been prepared starting from furfuryl alcohol and acetone. The method involves the diastereoselective [4+3]-cycloaddition of 2-[(benzyloxy)methyl]furan and 1,3-dibromo-2-oxyallyl cation giving adduct (±)-4 that was converted with high yield into (±)-(2RS,5RS,6SR)-5-azido-2-[(benzyloxy)methyl]-2,3,5,6-tetrahydro- 2,6-bis(hydroxymethyl)-4H-pyran-4-one ((±)-9). Ketone (±)-9 was then transformed with high selectivity into (±)-(2RS,4RS,5SR,6RS)-5-azido-2-[(benzyloxy)methyl]-2,3,5,6- tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H- pyran-2-methanol (±)-3 that was resolved by the Alexakis-Mangeney method (column chromatography of aminals derived from (1R,2R)-1,2-diphenylethylenediamine). The absolute configuration of (-)-3 was established by circular dichroism and the Dale-Mosher method on derivatives.
