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
• Article Data: 18

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

• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 122743-18-4 methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate 
• 100-47-0 benzonitrile 
• 235432-35-6 3-N-benzoyl-4-phenyl-(4S,5R)-2,2-dioxo-1,2,3-oxathiazolidine methyl ester 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 144541-45-7 methyl (2S,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 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 
• 146848-90-0 (2S,3S)-(-)-isobutyl N-benzoyl-3-phenylisoserinate 
• 146848-88-6 (2S,3S)-(+)-isobutyl 3-azido-2-hydroxy-3-phenylpropionate 
• 146848-87-5 (+)-isobutyl (2S,3R)-3-phenylglycidate 
• 161513-45-7 tert-butyl (2S,3S,αS)-3--2-hydroxy-3-phenylpropionate 

Downstream Products

• 153652-62-1 C₄₇H₄₉NO₁₃ 
• 158800-38-5 C₄₇H₄₉NO₁₃ 
• 158722-23-7 7-(triethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydrooxazol-5-yl)carbonyl]baccatin 
• 33069-62-4 taxol 
• 201047-50-9 (E)-3-((4S,5S)-2,4-Diphenyl-4,5-dihydro-oxazol-5-yl)-acrylic acid ethyl ester 
• 395664-49-0 C₃₁H₃₃NO₆ 
• 395664-51-4 C₃₁H₃₃NO₆ 
• 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 
• 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.

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.