220272-52-6

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 
• 124356-91-8 (4S,2'S,3'R)-3-(2'-methyl-3'-hydroxypentanoyl)-4-benzyl-2-oxazolidinone 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 1401455-67-1 (R)-benzyl 2-methyl-3-oxopentanoate 
• 78433-60-0 (2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-methylpentyl 4-methylbenzenesulfonate 
• 220272-62-8 (S)-4-Benzyl-3-[(2S,3R,4R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-heptanoyl]-oxazolidin-2-one 
• 186489-73-6 (R)-4-Benzyl-3-[(2R,3S,4R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-heptanoyl]-oxazolidin-2-one 
• 888947-95-3 5-[3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentylsulfanyl]-1-phenyl-1H-tetrazole 

Relevant academic research and scientific papers

A dehydratase domain in ambruticin biosynthesis displays additional activity as a Pyran-forming Cyclase

Hydropyran rings are a common structural motif in reduced polyketides. Information on their biosynthetic formation and particularly the biochemical characterization of the responsible enzymes has only been reported in few cases. The dehydratase domain AmbDH3 from the ambruticin polyketide synthase was investigated. Through in vitro assay of the recombinant domain with synthetically-derived substrate surrogates, it was shown that it has a second catalytic activity as a cyclase that performs oxa-conjugate addition. Probing AmbDH3 with synthetic substrate analogues revealed stereo-selectivity and substrate tolerance in both substeps. This is the first characterization of a pyran-forming cyclase from a cis-AT PKS system and the first report of a polyketide synthase domain with this kind of dual activity. Finally, it was revealed that this domain shows potential for application in chemo-enzymatic synthesis.

Racemization of α-Alkyl-β-Keto Esters and Enantioselective Total Synthesis of Two C-2′′′Epimers of Plant Glycerolipid Santinol C

It is broadly believed that optically active α-alkyl-β-keto esters racemize very quickly. Nevertheless, no one really knows how fast the racemization is. In fact, such species are hardly attainable to date. Now, a facile entry to these greatly understudied esters has been found and their racemization has been studied for the first time. The results showed that under neutral or slightly acidic conditions such species were much more stable than one might expect, though they did racemize rapidly under basic conditions. In light of the new findings, santinol C was also synthesized in enantiopure forms.

Precursor directed biosynthesis of an orthogonally functional erythromycin analogue: Selectivity in the ribosome macrolide binding pocket

The macrolide antibiotic erythromycin A and its semisynthetic analogues have been among the most useful antibacterial agents for the treatment of infectious diseases. Using a recently developed chemical genetic strategy for precursor-directed biosynthesis and colony bioassay of 6-deoxyerythromycin D analogues, we identified a new class of alkynyl- and alkenyl-substituted macrolides with activities comparable to that of the natural product. Further analysis revealed a marked and unexpected dependence of antibiotic activity on the size and degree of unsaturation of the precursor. Based on these leads, we also report the precursor-directed biosynthesis of 15-propargyl erythromycin A, a novel antibiotic that not only is as potent as erythromycin A with respect to its ability to inhibit bacterial growth and cell-free ribosomal protein biosynthesis but also harbors an orthogonal functional group that is capable of facile chemical modification.

Linear aglycones are the substrates for glycosyltransferase DesVII in methymycin biosynthesis: Analysis and implications

The two essential structural components of macrolide antibiotics are the polyketide aglycone and the appended sugars. The aglycone formation is catalyzed by polyketide synthase (PKS), and glycosylation is catalyzed by an appropriate glycosyltransferase. A

Enantiospecific synthesis of tetrasubstituted δ-lactones

For investigations concerning the selectivity of polyketide synthases (PKSs) which have been rationally engineered through genetic techniques the synthesis of substituted δ-lactones is of great importance. An enantiospecific route towards eight of the possible sixteen stereoisomers was developed which is also readily adaptable for the introduction of alkyl modifications and isotopic labels.

10. The enantioselective synthesis of the 'Southern Part' of soraphen A

Using a series of enantioselective aldol condensations followed by an ester enolate addition, the cyclic hemiacetal 2 was prepared stereospecifically. Hemiacetal 2 represents the synthetically most challenging 'southern part' of the antifungal macrolide s