201933-48-4

Upstream product

• 183888-74-6 (S)-4-{(1S)-2-[(1,1-dimethylethyl)diphenylsilyloxy]-1-(hydroxy)ethyl}-2,2-dimethyl-1,3-dioxolane 
• 91274-05-4 (2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 114185-07-8 ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 

Downstream Products

• 374556-99-7 methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-D-glycero-D-allo-heptafuranosiduronic acid 
• 374557-00-3 methyl (5R)-5-C-[(2'R,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 201933-46-2 (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane 
• 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 
• 201933-52-0 methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 374556-93-1 (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)butane-1,2-diol 

Relevant academic research and scientific papers

Synthetic studies towards diazepanone scaffolds

The synthesis of new enantiopure polyfunctionalised diazepanone scaffolds is described. The key steps involve the opening of an azido-epoxide C4 building block derived from l-ascorbic or d-isoascorbic acid by a l-serine derivative followed by a lactonisation-lactamisation two-step sequence.

Efficient synthesis of polyfunctionalised enantiopure diazepanone scaffolds

The synthesis of polyfunctionalised enantiopure 1,4-diazepan-3-one scaffolds from l-serine derivatives and azidoepoxides readily available from either l-ascorbic or d-isoascorbic acid, allowing access to various configurations at chiral centres, is descri

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.