149140-54-5

Usage

Uses

Used in Organic Synthesis:
(3R-cis)-4-Phenyl-3-[(triethylsilyl)oxy]-2-azetidinone is used as a synthetic building block for the development of new organic compounds. Its unique structure allows for the formation of a wide range of molecules with diverse applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3R-cis)-4-Phenyl-3-[(triethylsilyl)oxy]-2-azetidinone is used as a key intermediate in the synthesis of various drugs. Its ability to form a variety of organic compounds makes it a valuable asset in the development of new medications with improved efficacy and reduced side effects.
Used in Chemical Research:
(3R-cis)-4-Phenyl-3-[(triethylsilyl)oxy]-2-azetidinone is also used in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methods. Its unique structure provides researchers with valuable insights into the behavior of similar compounds and helps in the design of more efficient and selective synthetic routes.
Used in Material Science:
In the field of material science, (3R-cis)-4-Phenyl-3-[(triethylsilyl)oxy]-2-azetidinone can be used as a component in the development of new materials with specific properties. Its versatility in forming different organic compounds allows for the creation of materials with tailored characteristics, such as improved mechanical strength, thermal stability, or chemical resistance.

InChI:InChI=1/C15H23NO2Si/c1-4-19(5-2,6-3)18-14-13(16-15(14)17)12-10-8-7-9-11-12/h7-11,13-14H,4-6H2,1-3H3,(H,16,17)/t13-,14+/m0/s1

Upstream product

• 994-30-9 triethylsilyl chloride 
• 132127-34-5 (3R,4S)-3-hydroxy-4-phenylazetidin-2-one 
• 350583-44-7 methyl (2R,3S)-3-amino-3-phenyl-2-(triethylsilyloxy)propanoate 
• 99458-15-8 Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 350583-35-6 (2R,3S)-3-Azido-3-phenyl-2-triethylsilanyloxy-propionic acid methyl ester 
• 144790-01-2 (3R-cis)-3-acetyloxy-4-phenyl-2-azetidinone 
• 208848-58-2 Acetic acid (3R,4S)-1-[(S)-1-(4-methoxy-phenyl)-propyl]-2-oxo-4-phenyl-azetidin-3-yl ester 
• 132127-31-2 (3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one 
• 288-32-4 1H-imidazole 
• 930-21-2 2-azetidinone 

Downstream Products

• 149198-47-0 tert-butyl (3R,4S)-2-oxo-4-phenyl-3-(triethylsilyloxy)azetidine-1-carboxylate 
• 160084-30-0 (3R,4S)-1-Cyclohexanecarbonyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one 
• 161518-61-2 (3R,4S)-cis-1-benzoyl-3-O-(triethylsilyl)-4-phenylazetidin-2-one-N₁-¹⁴C 
• 149249-91-2 (3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone 
• 355113-95-0 (3R,4S)-1-neopentylcarbonyl-4-phenyl-3-triethylsilyloxyazetidin-2-one 
• 618886-87-6 (3R,4S)-1-(3-iodobenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one 
• 393547-86-9 (3R,4S)-2-Oxo-4-phenyl-3-triethylsilanyloxy-azetidine-1-carboxylic acid isopropyl ester 
• 175718-56-6 (3R,4S)-2-Oxo-4-phenyl-3-triethylsilanyloxy-azetidine-1-carboxylic acid butyl ester 
• 355113-96-1 (3R,4S)-1-Cyclobutanecarbonyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one 
• 661489-77-6 C₅₇H₈₃NO₁₇Si₂ 
• 661489-74-3 C₅₈H₈₅NO₁₇Si₂ 
• 618886-85-4 2-debenzoyl-2-(3-ethenylbenzoyl)-3'N-debenzoyl-3'N-(3-iodobenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel 

Relevant academic research and scientific papers

Syntheses and biological evaluation of C-30-N-acyl modified taxane analogues from 1-deoxybaccatin-VI

A series of side-chain modified taxane analogues were synthesized and their in vitro anticancer activities against four human cancer cell lines: MDA-MB-231 (human breast cancer), PC-3 (human prostatic cancer), HepG2 and H460 (human hepatoma) were studied.

A four-membered ring taxol alkane side chain compound preparation method

The invention relates to a preparation method of a four-membered ring taxane side chain compound, and belongs to the field of synthesis of medicines. The four-membered ring taxane side chain compound as shown in the formula I is prepared from a compound as shown in the formula II. The preparation method overcomes the defects of being low in reaction yield and complicated in postprocessing, and needing column chromatography to obtain a purified product in the industrial production in the prior art, and has the advantages of simple equipment, easiness in operation, higher yield, and easiness in industrial production.

A chiral four membered ring taxol alkane side chain compound preparation method

The invention relates to a preparation method of a chiral four-membered-ring taxane side chain compound and belongs to the field of pharmaceutical synthesis. The chiral four-membered-ring taxane side chain compound as shown in the formula I is prepared from a compound as shown in the formula II through a cyclization reaction. The method overcomes the defects of the relatively high cost of (2R,3S)-phenyl isoserine methyl ester in the prior art, and has the advantages of low cost of the used achiral material, simple equipment, easiness in operation, higher yield, and easiness in industrial production.

Total synthesis of a library of designed hybrids of the microtubule-stabilising anticancer agents taxol, discodermolide and dictyostatin

A hybrid library of the marine natural products dictyostatin and discodermolide, incorporating the taxol or taxotere side chains, were synthesised; preliminary biological evaluation in the PANC-1 cancer cell line revealed significant antiproliferative activity, demonstrating that a macrolide scaffold is an effective surrogate for the baccatin core of taxol.

Semisynthesis of flexible 5,7-dideoxypaclitaxel derivatives from Taxine B

Two new 5,7-dideoxypaclitaxel derivatives with flexible C-rings have been prepared starting from Taxine B, an alkaloid isolated from the leaves of Taxus baccata. Both derivatives lack the oxetane ring present in the antitumor agent paclitaxel, but possess an oxygenated 4β-substituent as a substitute for the oxetane ring oxygen atom. These derivatives provide additional information about the importance of this oxygen atom for cytotoxic activity.

A convenient synthesis of the paclitaxel side-chain via a diastereoselective Staudinger reaction

The N-benzylidene dexivative of (S)-(-)-1-(p-mathoxyphenyl)propyl-1- amine, obtained by a new resolution procedure, exhibits moderate selectivity in the reaction with 2-acetoxyketene; the (S)-(-)-1-(p-methoxyphenyl)propyl group can be oxidatively cleaved from the resultant β-lactam, an important precursor for taxane semi-synthesis.

Deoxy taxols

Rg is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, or a radical of the formula --W--Rx in which W is a bond, C2-6 alkenediyl, or --(CH2)t --, in which t is one to six; and Rx is naphthyl, phenyl, or heteroaryl, and furthermore Rx can be optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or --CF3 groups; R2 is --OCOR, H, OH, --OR, --OSO2 R, --OCONRo R, --OCONHR, --OCOO(CH2)t R, or --OCOOR; and R and Ro are independently C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, C2-6 alkynyl, or phenyl, optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or --CF3 groups. Further provided by this invention are pharmaceutical formulations and intermediates for the the preparation of deoxy taxols of formula I. A method of treating mammalian tumors using a compound of formula I is also provided.

Synthesis of carbon-14 labeled Taxolo (paclitaxel)

Reductive cleavage of the C13 side chain of Taxolo (1, paclitaxel) followed by regioselective silylation gave 7-triethylsilylbaccatin III (4). 3-O-Triethylsilylation of 5 and subsequent reaction with benzoyl chloride-C7-14C gave azetidinone 7. Coupling of 4 and 7 followed by deprotection gave 1.26 g of Taxol-N3'14C (11) having a specific activity of 26.5 mCi/mmol and a radiochemical purity of 95%.

Studies on the photochemistry of taxol

Irradiation of taxol at 280 nm in a Rayonet reactor yielded a novel pentacyclic derivative containing a new bond between C-3 and C-11. The proposed mechanism involves a triplet intermediate and the first event of the oxa-di-π-methane rearrangement. Taxane

A highly efficient route to taxotere by the β-lactam synthon method

Taxotere, a highly promising anticancer drug, is synthesized through an efficient coupling of 7,10-diTroc-10-deacetylbaccatin III with enantiomerically pure (3R,4S)-1-tBOC-3-EEO- 4-phenylazetidin-2-one which is obtained via chiral ester enolate - imine cyclocondensation.