201933-46-2

Upstream product

• 374556-93-1 (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)butane-1,2-diol 
• 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 

Downstream Products

• 960243-43-0 C₃₅H₄₈N₄O₅Si 
• 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 
• 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 
• 1202878-73-6 (2R,3R)-3-amino-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 
• 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 

Relevant academic research and scientific papers

Nucleophilic opening of an epoxide by a masked glycine anion equivalent: A route to C-glycosyl amino acids

An efficient method has been developed for the synthesis of C-glycosyl amino acids through a tandem nucleophilic opening-cyclization of an l-ido-bisepoxide with the anion of Sch?llkopf's bislactim. A masked amine was introduced at the CH2C1-position of the resulting compound. The products are enantiopure polyfunctionalized intermediates, suitable for further synthesis of antibacterial compounds.

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.