64190-49-4

Upstream product

• 90865-69-3 (3S)-4-Benzyloxy-3-methyl-butyraldehyde 
• 75-16-1 methylmagnesium bromide 
• 252873-91-9 4-(R)-benzyloxymethyl-β-propiolactone 
• 124-38-9 carbon dioxide 
• 63930-47-2 (2R)-3-bromo-2-[(methylpropyloxy)methyl]benzene 
• 56850-58-9 methyl (2R)-3-(benzyloxy)-2-methylpropanoate 
• 63930-46-1 (S)-3-benzyloxy-2-methylpropan-1-ol 
• 90809-23-7 (1E,3S)-4-(Benzyloxy)-N,N-diethyl-3-methylbut-1-enylamine 
• 91458-94-5 (1E,3R)-4-(Benzyloxy)-N,N-diethyl-3-methylbut-1-enylamine 
• 132364-34-2 (E)-4-(Diethylamino)-2-methylbut-2-en-1-ol 
• 90809-16-8 4-<(E)-4-(Benzyloxy)-3-methylbut-2-enyl>morpholine 
• 90809-27-1 4-<(1E,3R)-4-(Benzyloxy)-3-methylbut-1-enyl>morpholine 
• 90809-13-5 (E)-4-(Benzyloxy)-N,N-diethyl-3-methylbut-2-enylamine 
• 132364-36-4 (E)-4-Morpholino-2-methylbut-2-en-1-ol 

Downstream Products

• 132364-41-1 (3S)-4-(Benzyloxy)-3-methyl-N-<(R)-α-methyl-4-nitrobenzyl>butanamide 
• 181116-43-8 (1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate 
• 1252651-78-7 C₂₂H₂₅NO₄ 
• 1252651-69-6 C₂₂H₂₄N₄O₄ 
• 1252651-62-9 C₁₃H₁₈N₄O₂ 
• 181230-42-2 (2S,3S)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid 
• 181116-44-9 (2R,3S)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid 

Relevant academic research and scientific papers

Chemical synthesis enables biochemical and antibacterial evaluation of streptolydigin antibiotics

Inhibition of bacterial transcription represents an effective and clinically validated anti-infective chemotherapeutic strategy. We describe the evolution of our approach to the streptolydigin class of antibiotics that target bacterial RNA polymerases (RN

Synthesis of streptolydigin, a potent bacterial RNA polymerase inhibitor

Streptolydigin is a highly potent, broad-spectrum antibiotic produced by Streptomyces lydicus, which inhibits bacterial RNA polymerase. We describe the first synthesis of streptolydigin, which was assembled in a highly convergent and fully stereocontrolle

SN2 ring opening of β-lactones: An alternative to catalytic asymmetric conjugate additions

Merging catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions with ensuing Grignard-mediated ring opening of the derived enantiomerically enriched β-lactones is presented as a generally useful asymmetric synthesis of β-disubstituted

A new synthesis of (S)-β-methyl-γ-butyrolactone and (S)-4-benzyloxy-3-methylbutanoic acid

A stereoselective synthesis of (S)-β-methyl-γ-butyrolactone [(S)-4,5-dihydro-4-methyl-2(3H)-furanone, 1] and of (S)-4-benzyloxy-3-methylbutanoic acid (2) is described. Both compounds are prepared starting from inexpensive L-ethyl lactate with overall yields of 26% and 30%, respectively. The products are valuable chiral building blocks.

Synthesis of Optically Active Bifunctional Isoprenoid Building Blocks by Rhodium(I)-Catalyzed Asymmetric Allylamine to Enamine Isomerization

The application of the known asymmetric allylamine to enamine isomerization methodology to bifunctional C5-isoprenoid allylic amines of types IId and IIe (Scheme 1) is described.It is shown that a number of such substrates can be isomerized with enantioselectivities of >90percent ee using cationic RhI complexes containing (6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine) (BIPHEMP; 9) as asymmetry-inducing ligand (Scheme 2, Tables 1 and 2).Synthetically most useful is the isomerization of the benzyloxy derivative 10a into the (E)-enamine 11a.This isomerization proceeds with very high enantioselectivity (98-99percent ee) and affords, after enamine hydrolysis, the optically active 4-(benzyloxy)-3-methylbutanals ((R)- or (S)-12) in chemical yields of ca. 90percent.In conjunction, a short synthetic route to the starting material 10a has been developed which has a Pd-catalyzed amination of isoprene epoxide (30) as the key step.Thus, convenient and practical access to the optically active aldehydes (R)- and (S)-12 is now at hand.These aldehydes are useful optically active bifunctional building blocks for isoprenoid homologation.