149249-91-2

Basic information

• Product Name: (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone
• Synonyms: PACLITAXEL SIDE CHAIN NO 2;(3R,4S)-1-Benzoyl-4-Phenyl-3-[(Triethylsilyl)Oxy]-2-AzetidinoneCasNo.;(3R,4S)-1-BENZOYL-3-[(TRIETHYLSILYS)OXY]-4-PHENYL-2-AZETIDINONE;(3R,4S)-1-Benzoyl-3-[(Triethyl;PACLITAXEL SIDE CHAIN/(3R,4S)-1-BENZOYL-3-[(TRIETHYLSILYL)OXY]-4-PHENYL-2-PHENYL-2-AZETIDINONE;(3R,4S)-1-benzoyl-4-phenyl-3- (triethylsilyloxy)azetidin-2-one;(3R,4S)-3-triethylsilanyloxy-4-phenyl-N-benzoyl-2-azetidinone;(3R,4S)-1-BENZOYL-3-[(TRIETHYLSILYL)OXY]-4-PHENYL-2-AZETIDINONE
• CAS NO: 149249-91-2
• Molecular Formula: C₂₂H₂₇NO₃Si
• Molecular Weight: 381.54
• Mol File: 149249-91-2.mol

Chemical Properties

• Boiling Point: 467.227 °C at 760 mmHg
• Flash Point: 236.371 °C
• Appearance: /
• Density: 1.12
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane, Ether, Ethyl Acetate, Methanol
• PKA: -4.66±0.60(Predicted)
• CAS DataBase Reference: (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone(149249-91-2)
• EPA Substance Registry System: (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone(149249-91-2)

Safety Data

• Hazardous Substances Data: 149249-91-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone is used as an intermediate in the synthesis of 10-O-[(2R,3S)-3-(Benzoylamino)-2-hydroxy-3-phenylpropanoyl]-10-O-deacetylpaclitaxel (B207800), which is an impurity in the synthesis of Paclitaxel (P132500). Paclitaxel is a widely used antineoplastic agent, effective against various types of cancer.
Used in Cancer Treatment:
(3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone, through its role in the synthesis of Paclitaxel, contributes to the treatment of patients with lung, ovarian, breast cancer, head and neck cancer, and advanced forms of Kaposi's sarcoma. Paclitaxel's mechanism of action involves stabilizing microtubules and preventing cell division, thereby inhibiting tumor growth.
Used in Research and Development:
The compound is also utilized in the study of the structure and function of microtubules and their interaction with tubulin, providing valuable insights into the mechanisms underlying the action of antineoplastic drugs and potentially leading to the development of novel therapeutic agents.

InChI:InChI=1/C22H27NO3Si/c1-4-27(5-2,6-3)26-20-19(17-13-9-7-10-14-17)23(22(20)25)21(24)18-15-11-8-12-16-18/h7-16,19-20H,4-6H2,1-3H3/t19-,20+/m0/s1

Upstream product

• 98-88-4 benzoyl chloride 
• 149140-54-5 (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one 
• 144790-01-2 (3R-cis)-3-acetyloxy-4-phenyl-2-azetidinone 
• 132127-34-5 (3R,4S)-3-hydroxy-4-phenylazetidin-2-one 
• 994-30-9 triethylsilyl chloride 
• 350583-35-6 (2R,3S)-3-Azido-3-phenyl-2-triethylsilanyloxy-propionic acid methyl ester 
• 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 
• 208848-58-2 Acetic acid (3R,4S)-1-[(S)-1-(4-methoxy-phenyl)-propyl]-2-oxo-4-phenyl-azetidin-3-yl ester 

Downstream Products

• 160582-82-1 C₆₄H₈₁NO₁₄Si₂ 
• 160582-79-6 C₆₁H₈₁NO₁₄Si₂ 
• 155371-52-1 2-hexahydro-2',7-bis(triethylsilyl)paclitaxel 
• 175275-04-4 Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-2-yl ester 
• 155192-71-5 Benzoic acid (1S,2S,9R,10R,13S)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-2-yl ester 
• 153145-54-1 C₆₁H₇₃NO₁₅Si 
• 153280-62-7 C₅₁H₆₃NO₁₁Si 
• 149705-85-1 7-deoxypaclitaxel 
• 135365-62-7 1-hydroxy-7β-triethylsilyloxy-9-oxo-10β-acetyloxy-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-benzoylamino-2-triethylsilyloxy-3-phenylpropanoate] 
• 33069-62-4 taxol 

Relevant articles and documents

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.

Phosphonooxy and carbonate derivatives of taxol

The present invention is directed to novel taxol derivatives useful as anti-tumor agents. Also provided by this invention is pharmaceutical formulations and methods of treating mammalian tumors with the compounds of this invention.