412917-35-2

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 684270-34-6 benzyl N-[(1S)-1-(hydroxymethyl)-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate 
• 501-53-1 benzyl chloroformate 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 

Downstream Products

• 1476733-07-9 (S)-benzyl 4-acryloyl-2,2-dimethyloxazolidine-3-carboxylate 

Relevant academic research and scientific papers

Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers

The proposed diastereoisomers (1 a–d) together with their C8′-epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio- and stereocontrolled gold(I)-catalyzed N-glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be of opposite configuration.

Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling

The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis -oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

An alkylidene carbene C-H insertion strategy for the enantioselective synthesis of α,α-dialkyl-α-amino acids

A synthesis of the α,α-dialkyl-α-amino acid (1S,3R)-2,5-methano-leucine has been achieved using an alkylidene carbene 1,5-C-H insertion reaction as a key step. Treatment of the ketone 11 with 1.2 equivalents of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the cyclopentene 13 in 62% yield. The enantiomeric excess of the product 18 was determined to be >95% by chiral HPLC (Chiracel OD column).