374072-95-4

Upstream product

• 201158-30-7 phenylmethyl-(5S,4R)-4-(N-methoxy-N-methyl-carbamoyl)-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate 
• 1402887-64-2 C₁₄H₂₀N₂O₅ 
• 5618-95-1 (2R,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid 
• 84449-06-9 methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate 
• 75-16-1 methylmagnesium bromide 
• 374072-93-2 phenylmethyl-(5S,4R)-4-(methoxycarbonyl)-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 374073-20-8 N-((2S,3R,4R,5R)-4,5-dihydroxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide 
• 374073-04-8 N-((2S,3R,4R,5R)-4-hydroxy-5-methoxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide 
• 1402887-66-4 C₂₁H₃₃NO₅Si 
• 1402887-65-3 C₁₅H₁₉NO₅ 
• 374073-08-2 (4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 374072-97-6 ethyl (2S,3R)-3-{(4R,5S)-2,2,5-trimethyl-3-[benzyloxycarbonyl](1,3-oxazolidin-4-yl)}-3-hydroxy-2-methoxy-butanoate 
• 374072-99-8 ethyl (2R,3R)-3-{(4R,5S)-2,2,5-trimethyl-3-[benzyloxycarbonyl](1,3-oxazolidin-4-yl)}-3-hydroxy-2-methoxy-butanoate 

Relevant academic research and scientific papers

Total synthesis of (-)-lemonomycin

When life gives you lemons: An efficient and convergent enantioselective total synthesis of (-)-lemonomycin, which shows potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF), is presented. The key reaction steps are a Hosomi-Sakurai-type cyclization, a thermodynamically controlled Pictet-Spengler reaction, and a glycosidation reaction with lemonose (see scheme). Copyright

Enantioselective total synthesis of callipeltoside A: two approaches to the macrolactone fragment

The enantioselective total synthesis of callipeltoside A is described. Two syntheses of the macrolactone subunit are included: the first relies upon an Ireland-Claisen rearrangement to generate the trisubstituted olefin geometry and the second utilizes an enantioselective vinylogous aldol reaction for this purpose. Enantioselective syntheses of the sugar and chlorocyclopropane side chain fragments are also disclosed. The relative and absolute stereochemistry of this natural product was determined by fragment coupling with the two enantiomers of the side chain fragment.

An aldol-based approach to the asymmetric synthesis of L-callipeltose, the deoxyamino sugar of L-callipeltoside A.

[reaction: see text] The L-callipeltose subunit of L-callipeltoside A has been synthesized in 10 steps and 13% overall yield from D-threonine. The key steps are a highly diastereoselective Felkin anti aldol addition to a methyl ketone and a selective methylation of a secondary alcohol in the presence of a secondary carbamate.