218766-12-2

Upstream product

• 112418-19-6 (R)-2-N-tert-butoxycarbonylamino-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester 
• 217661-62-6 [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 124085-68-3 tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 218766-10-0 (1R,2R)-2-(Benzhydrylidene-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-propan-1-ol 
• 208253-69-4 (R)-2-(Benzhydrylidene-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 218766-11-1 (1R,2R)-2-amino-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol 

Downstream Products

• 109760-77-2 D-threo-1-ethylendioxyphenyl-2-decanoylamino-3-pyrrolidinopropanol 
• 193545-88-9 (1R,2R)-2-Amino-3-pyrrolidino-1-phenyl-1-propanol 
• 218766-25-7 (1R,2R)-2-Amino-1-phenyl-3-piperidin-1-yl-propan-1-ol 
• 218766-24-6 (1R,2R)-2-Amino-1-phenyl-3-thiomorpholin-4-yl-propan-1-ol 
• 218766-22-4 (4R,5R)-5-Phenyl-4-pyrrolidin-1-ylmethyl-oxazolidin-2-one 
• 218766-21-3 (4R,5R)-5-Phenyl-4-piperidin-1-ylmethyl-oxazolidin-2-one 
• 218766-16-6 (4R,5R)-5-Phenyl-4-thiomorpholin-4-ylmethyl-oxazolidin-2-one 
• 127870-56-8 (4R,5R)-4-Hydroxymethyl-5-phenyl-oxazolidin-2-one 

Relevant academic research and scientific papers

Total synthesis of cyclomarins A, C and D, marine cyclic peptides with interesting anti-tuberculosis and anti-malaria activities

Cyclomarins are cyclic heptapeptides containing four unusual amino acids. New synthetic protocols toward their synthesis have been developed, leading to the synthesis and biological evaluation of three natural occurring cyclomarins. Interestingly, cyclomarins address two completely different targets: Clp C1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp3Ase of Plasmodium falciparum. Therefore, cyclomarins are interesting lead structures for the development of drugs against tuberculosis and malaria.

Glycosyltransferase inhibitors: Synthesis of D-threo-PDMP, L-threo- PDMP, and other brain glucosylceramide synthase inhibitors from D- or L- serine

The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2- decanoylamino-3-N-morpholino-1-propanol (L-threo-PDMP) (1a) from L-serine, and the enantiomer (LR,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (1b) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the β-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure 1b in high yield after six steps. Three other D- threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D- threo-PDPP (1e). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.