146848-91-1

Basic information

• Product Name: 5-Oxazolecarboxylic acid, 4,5-dihydro-2,4-diphenyl-, methyl ester, (4S,5R)-
• CAS NO: 146848-91-1
• Molecular Formula: C17H15NO3
• Molecular Weight: 281.311
• Mol File: 146848-91-1.mol

Chemical Properties

• CAS DataBase Reference: 5-Oxazolecarboxylic acid, 4,5-dihydro-2,4-diphenyl-, methyl ester, (4S,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Oxazolecarboxylic acid, 4,5-dihydro-2,4-diphenyl-, methyl ester, (4S,5R)-(146848-91-1)
• EPA Substance Registry System: 5-Oxazolecarboxylic acid, 4,5-dihydro-2,4-diphenyl-, methyl ester, (4S,5R)-(146848-91-1)

Safety Data

• Hazardous Substances Data: 146848-91-1(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 158722-22-6 (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid 
• 122743-18-4 methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate 
• 100-47-0 benzonitrile 
• 2935-35-5 (S)-2-phenylglycine 
• 129866-71-3 Methyl (2S,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 263247-50-3 (R)-3-benzamido-3-phenylpropanoic acid 
• 83649-48-3 (R)-3-amino-3-phenylpropionic acid hydrochloride 
• 146848-90-0 (2S,3S)-(-)-isobutyl N-benzoyl-3-phenylisoserinate 
• 136561-53-0 (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid 
• 19190-80-8 methyl trans-3-phenylglycidate 
• 7309-55-9 (2S,3S)-N-benzoyl-3-phenylisoserine 
• 146848-89-7 (2S,3S)-(+)-isobutyl 3-azido-2-benzoxy-3-phenylpropionate 
• 146848-88-6 (2S,3S)-(+)-isobutyl 3-azido-2-hydroxy-3-phenylpropionate 

Downstream Products

• 395664-70-7 (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (4S,4aR)-6,6,8-trimethyl-1-oxo-1,3,4,4a,5,6,7,9-octahydro-2-oxa-cyclopenta[f]azulen-4-yl ester 
• 395664-51-4 C₃₁H₃₃NO₆ 
• 395664-49-0 C₃₁H₃₃NO₆ 
• 33069-62-4 taxol 
• 158722-23-7 7-(triethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydrooxazol-5-yl)carbonyl]baccatin 
• 158800-38-5 C₄₇H₄₉NO₁₃ 
• 153652-62-1 C₄₇H₄₉NO₁₃ 
• 201047-50-9 (E)-3-((4S,5S)-2,4-Diphenyl-4,5-dihydro-oxazol-5-yl)-acrylic acid ethyl ester 
• 374536-37-5 (4S,5R)-2,4-diphenyl-4,5-dihydro-oxazol-5-carboxylic acid (15-O-t-butyl-dimethylsilyl-lactarorufin B)-8-epi-8-yl ester 
• 374536-35-3 (4S,5R)-2,4-diphenyl-4,5-dihydro-oxazol-5-carboxylic acid (15-O-t-butyldimethylsilyl-lactarorufin B)-8-yl ester 

Relevant articles and documents

Paclitaxel compounds with modified C-13 and C-14 position structure and preparing method of paclitaxel compounds

The invention relates to a paclitaxel analogue with modified C-13 and C-14 positions and a preparing method of the paclitaxel analogue. The structural formula of the analogue is shown in the description. Different side chains are introduced into the C-13 position and the C-14 position of taxanes of 1-dehydroxybaccatin VI, the annular framework and necessary functional groups of paclitaxel are reserved, paclitaxel compounds are enriched, the obtained compounds have the natural anti-cancer biological activity of natural paclitaxel, certain application prospects on the aspect of reducing the toxic and side effects of natural paclitaxel are achieved, and meanwhile it is highly beneficial for studying the activity structure-function relationship of the compounds. The compounds a, b, c, d and taxol have a suppressing effect on the in-vitro proliferation of the A 549 lung cancer cells, A 2780 ovarian carcinoma cells and HL-60 promyelocytic leukemia cells of the human body.

Enantioselective synthesis of 1-aryl-2-propenylamines: A new approach to a stereoselective synthesis of the Taxol side chain

A variety of substituted 1-aryl-2-propenylamines of high enantiomeric purity were prepared via lipase-catalysed resolution of the corresponding racemates. (R)-1-Phenyl-2-propenylamine was further synthesised into (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoic acid methyl ester, the side chain of Taxol.

Synthesis and Antifeedant Properties of N-Acylphenylisoserinates of Lactarius Sesquiterpenoid Alcohols

The esterification of various sesquiterpenoid alcohols of Lactarius origin with N-benzoyl-[2R,3S]-phenylisoserine (side chain of Taxol), N-acetyl-[2R,3S]-phenylisoserine and N-tert-butoxy-[2R,3S]-phenylisoserine (side chain of Taxotere) produced compounds whose antifeedant properties against storage pests Tribolium confusum, Trogoderma granarium, Sitophylus granarius and Rhizoperta dominica were measured. The introduction of the ester moiety in these molecules, in comparison to original compounds, moderately enhanced their antifeedant activities, as well as changed their selectivity of activity towards the test insects.

Improved large-scale synthesis of phenylisoserine and the taxol C-13 side chain

Dihydrodihydroxycinnamic acids and their esters react with acetonitrile or benzonitrile in the presence of sulfuric acid to afford the corresponding syn-β-amino-α-hydroxypropionic acid derivatives. High yields and diastereoselectivity of this transformation allows preparation of various phenylisoserine derivatives on a practical scale.

A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates

Practical synthetic routes to β-amino-α-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of β-amino-α- keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation.

Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine

Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction.

Synthesis and antifeedant properties of N-benzoylphenylisoserinates of Lactarius sesquiterpenoid alcohols

The esterification of various sesquiterpenoid alcohols of Lactarius origin with N-benzoyl-[2R,3S]-phenylisoserine (side chain of Taxol) produced compounds whose antifeedant properties against storage pests Tribolium confusum, Trogoderma granarium and Sitophylus granarius were measured. The introduction of the taxol side chain in these molecules, in comparison to original compounds, moderately enhanced their antifeedant activities, as well as changed their selectivity of activity towards the test insects.

Efficient syntheses and ring-opening reactions of trans- and cis-Oxazoline-5-carboxylates

cis- and trans-Oxazoline-5-carboxylates were synthesized effeciently from isopropyl trans-cinnamate utilizing the sharpless AA reaction. trans-Oxazoline was much more reactive than the cis-isomer toward ring opening reactions. From ab initio molecular calculation, the cis-isomer was predicted to be less reactive than the trans-isomer by 2.7 kcal/mol. Both syn and anti acetylthio ester and anti diamino ester were synthesized from these cis- and trans- oxazoline-5-carboxylates.

Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere)

Reduction of methyl 3-chloro-2-oxo-3-phenylpropanoate with various reducing agents gave syn- and anti-3-chloro-2-hydroxy-3-phenylpropanoates 3, which underwent an efficient lipase-catalyzed resolution. All four diastereomers were subsequently converted to N-benzoyl-(2R,3S)-3-phenylisoserine methyl ester, C-13 side chain analogues of paclitaxel (Taxol).

Methods for the esterification of alcohols and compounds useful therefor as potential anticancer agents

The invention relates to a method for preparing an ester, by admixing a compound having the structure I or IV: with a base and an alcohol to produce an ester, wherein the alcohol is a precursor to Taxol and its analogs. The present invention also relates