201933-52-0

Upstream product

• 33985-40-9 (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 36468-53-8 β-D-ribofuranose 
• 374556-93-1 (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)butane-1,2-diol 
• 201933-46-2 (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane 
• 374556-97-5 methyl (4'S,5'S)-3'-methyl-5'-[methyl (4R)-2,3-O-isopropylidene-β-D-erythrofuranosid-4-yl]-2'oxooxazolidine-4'-carboxylate 
• 201933-55-3 methyl 6-deoxy-2,3-O-isopropylidene-6-(methylamino)-L-glycero-L-talo-heptafuranosiduronic acid 
• 201933-48-4 (2R,3R)-3-azido-4-tert-butyldiphenylsilyloxy-1,2-O-isopropylidenebutane-1,2-diol 
• 183888-74-6 (S)-4-{(1S)-2-[(1,1-dimethylethyl)diphenylsilyloxy]-1-(hydroxy)ethyl}-2,2-dimethyl-1,3-dioxolane 
• 201933-51-9 methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid 

Relevant academic research and scientific papers

Liposidomycins - Synthetic studies towards the ribosyldiazepanone moiety

A synthesis of the enantiopure 2-ribosyl-1,4-diazepan-3-one core of liposidomycins, a class of complex lipid nucleoside antibiotics, according to a flexible asymmetric synthesis strategy is described. It involves two building blocks, an enantiopure α-azido-β,γ-epoxybutanol readily available from L-ascorbic acid, and an α-ribosylamino acid obtained from D-ribose. Subsequent cyclization by regiospecific nucleophilic opening of the epoxide by the amino acid followed by peptidic coupling affords the target ribosyl diazepanone.

Access to enantiopure ribosyl-diazepanone core of liposidomycins

A convergent synthesis of the ribosyl-diazepanone core of liposidomycins, new nucleoside antibiotics, has been carried out via enantiomerically pure epoxide and α-ribosyl aminoacid, chiral key intermediates obtained from L-ascorbic acid and D-ribose, respectively.