374072-93-2

Upstream product

• 501-53-1 benzyl chloroformate 
• 5618-95-1 (2R,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid 
• 84449-06-9 methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 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 
• 374072-99-8 ethyl (2R,3R)-3-{(4R,5S)-2,2,5-trimethyl-3-[benzyloxycarbonyl](1,3-oxazolidin-4-yl)}-3-hydroxy-2-methoxy-butanoate 
• 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 
• 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 
• 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 
• 374072-95-4 phenylmethyl-(5S,4R)-4-acetyl-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate 
• 201158-30-7 phenylmethyl-(5S,4R)-4-(N-methoxy-N-methyl-carbamoyl)-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate 

Relevant academic research and scientific papers

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.