128329-72-6

Upstream product

• 64740-39-2 5-benzyloxypentanoic acid 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 4541-15-5 5-(benzyloxy)-1-pentanol 
• 111-29-5 1 ,5-pentanediol 

Downstream Products

• 129539-96-4 (2S-trans)-2,5-Dimethyl-1-<1-oxo-5-(phenylmethoxy)-pentyl>pyrrolidine 
• 128329-73-7 (+)-(4S)-3-(5'-(benzyloxy)pentanoyl)-4-isopropyl-1,3-oxazolidin-2-one 
• 142945-19-5 (4S)-4-benzyl-3-[5-(benzyloxy)pentanoyl]oxazolidin-2-one 
• 329914-29-6 (4R,5S)-3-(5-Benzyloxy-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 1000334-14-4 N-(3-(2-(acetylamino)ethyl)-4-hydroxy-2,3-dihydro-1H-inden-5-yl)-5-(benzyloxy)pentanamide 
• 928657-85-6 C₅₃H₆₁NO₁₀Si 
• 928657-92-5 C₅₃H₆₃NO₉Si 
• 928657-93-6 C₅₁H₆₃NO₇Si 
• 928657-94-7 C₅₃H₆₇NO₁₁S₂Si 
• 928657-96-9 C₇₂H₉₀N₂O₆Si₂ 
• 928657-97-0 C₅₈H₇₈N₂O₆Si₂ 
• 928657-98-1 C₅₈H₇₄N₂O₆Si₂ 
• 928657-99-2 C₆₀H₇₈N₂O₄Si₂ 
• 928658-04-2 C₅₁H₆₂N₂O₅Si 

Relevant academic research and scientific papers

Asymmetric radical addition of TEMPO to titanium enolates

A mild method for a-hydroxylation of N-acyl oxazolidinones by asymmetric radical addition of the 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO) radical to titanium enolates was developed. The high diastereoselectivity and broad scope of the reaction show synthetic utility for the a-hydroxylation of substrates that are not tolerant to strongly basic conditions.

A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates

A Ru-catalyzed direct thermal trifluoromethylation and perfluoroalkylation of N-acyloxazolidinones has been developed. The reaction is experimentally simple and requires inexpensive reagents while providing good yields of products with good levels of stereocontrol. Preliminary studies have shown notable compatibility with functional groups, aromatics, and certain heteroaromatic substituents. The described method provides a useful alternative for the synthesis of fluorinated materials in an experimentally convenient manner.

Total synthesis of (+)-nakadomarin A

The total synthesis of (+)-nakadomarin A is described. A three-component cycloaddition of a hydroxylamine, aldehyde, and cyclopropane to form a highly functionalized tetrahydro-1,2-oxazine serves as the foundation for this synthesis. The resulting oxazine

EPOTHILONE ANALOGUES

Epothilone analogues include a molecular scaffold which holds at least one segment of epothilone in a predetermined orientation and which rigidities a region between the macrolactone ring and the aromatic side-chain.

Structure-activity relationships of α-ketooxazole inhibitors of fatty acid amide hydrolase

A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1-napthyl, K, - 2.6 nM), with 5hh (aryl -3-ClPh, Ki = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, Ki = 3 nM, or 13d, 2-position OH, Ki = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of >100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.

The total synthesis and biological assessment of trans-epothilone A

The total synthesis of (12S,13S)-trans-epothilone A (1a) was achieved based on two different convergent strategies. In a first-generation approach, construction of the C(11)-C(12) bond by Pd0-catalyzed Negishi-type coupling between the C(12)-to-C(15) trans-vinyl iodide 5 and the C(7)-to-C(11) alkyl iodide 4 preceded the (nonselective) formation of the C(6)-C(7) bond by aldol reaction between the C(7)-to-C(15) aldehyde 25 and the dianion derived from the C(1)-to-C(6) acid 3. The lack of selectivity in the aldol step was addressed in a second-generation approach, which involved construction of the C(6)-C(7) bond in a highly diastereoselective fashion through reaction between the acetonide-protected C(l)-to-C(6) diol 31 ('Schinzer's ketone') and the C(7)-to-C(11) aldehyde 30. As part of this strategy, the C(11)-C(12) bond was established subsequent to the critical aldol step and was based on B-alkyl Suzuki coupling between the C(1)-to-C(11) fragment 40 and C(12)-to-C(15) trans-vinyl iodide 5. Both approaches converged at the stage of the 3-O, 7-O-bis-TBS-protected seco acid 27, which was converted to trans-deoxyepothilone A (2) via Yamaguchi macrolactonization and subsequent deprotection. Stereoselective epoxidation of the trans C(12)-C(13) bond could be achieved by epoxidation with Oxone in the presence of the catalyst 1,2:4,5-di-O-isopropylidene-L-erythro-2,3-hexodiuro-2,6-pyranose (42a), which provided a 8:1 mixture of 1a and its (12R,13R)-epoxide isomer 1b in 27% yield (54% based on recovered starting material). The absolute configuration of 1a was established by X-ray crystallography. Compound 1a is at least equipotent with natural epothilone A in its ability to induce tubulin polymerization and to inhibit the growth of human cancer cell lines in vitro. In contrast, the biological activity of 1b is at least two orders of magnitude lower than that of epothilone A or 1a.

Intermediates for the synthesis of epothilones and methods for their preparation

The invention relates to a method of synthesis for a compound of formula (I), wherein R is a heterocyclyl moiety and X1, X2, X3and X4are, independently of each other, protecting groups, which is appropriate for the synthesis of epothilone B and desoxyepothione B.

Synthesis of a C1-C21 subunit of the protein phosphatase inhibitor tautomycin: A formal total synthesis

The synthesis of a C1-C21 subunit of tautomycin is described. The convergent route employs enantioenriched allenylstannane and zinc reagents derived from (S)-3-butyn-2-ol methanesulfonate. These reagents react with appropriate aldehyde segments to yield s

Inhibition of matrix metalloproteinases by hydroxamates containing heteroatom-based modifications of the P1' group

In this study, structure-based drug design of matrix metalloproteinase inhibitors [human fibroblast collagenase (HFC), human fibroblast stromelysin (HFS), and human neutrophil collagenase (HNC)] was utilized in the development of potent hydroxamates which

Daphniphyllum Alkaloids. 13. Asymmetric Total Synthesis of (-)-Secodaphniphylline

(-)-Secodaphniphylline (1) has been prepared by total synthesis.The early stages of the synthesis were an asymmetric version of the previously published synthesis of methyl homosecodaphniphyllate (2).The necessary chirality was secured by an asymmetric Mi