208175-93-3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 208175-91-1 (2S,6S)-6-Hydroxymethyl-2-isopropoxy-dihydro-pyran-3-one 
• 14125-78-1 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-lyxo-hex-1-enitol 
• 151963-97-2 2-Propyl 6-O-acetyl-3,4-dideoxy-α-D-glycero-hexopyranosid-2-ulose 
• 114682-33-6 2-isopropyl 6-O-acetyl-3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-ulose 

Relevant academic research and scientific papers

Straightforward synthesis of a derivative of purpurosamine C from D- galactose

Purpurosamine C (1) is a component of the aminoglycoside antibiotic gentamicin C(1a). A derivative of 1 was synthesized from D-galactose via its 2-acetoxy-3,4,6-tri-O-acetyl glycal (3). Compound 3 undergoes glycosylation with 2-propanol in the presence of SnCl4, with two successive allylic rearrangements of the double bond to give isopropyl 6-O-acetyl-3,4-dideoxy- α-D-glycero-hex-3-enopyranosid-2-ulose (7). Compound 7 was hydrogenated, and O-deacetylated to afford 8. The free OH group of 8 was tosylated and substituted by azide, and the carbonyl function of the resulting ulose 10 reacted with hydroxylamine to give the E,Z-oximes (11,12). Highly diastereoselective reduction of the oxime acetate (13) by borane, which also reduced the azide function, led to the purpurosamine C derivative 14 (~40% yield from 3).