132127-31-2

Basic information

• Product Name: 2-Azetidinone, 4-phenyl-3-[[tris(1-methylethyl)silyl]oxy]-, (3R,4S)-
• CAS NO: 132127-31-2
• Molecular Formula: C18H29NO2Si
• Molecular Weight: 319.519
• Mol File: 132127-31-2.mol

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 4-phenyl-3-[[tris(1-methylethyl)silyl]oxy]-, (3R,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 4-phenyl-3-[[tris(1-methylethyl)silyl]oxy]-, (3R,4S)-(132127-31-2)
• EPA Substance Registry System: 2-Azetidinone, 4-phenyl-3-[[tris(1-methylethyl)silyl]oxy]-, (3R,4S)-(132127-31-2)

Safety Data

• Hazardous Substances Data: 132127-31-2(Hazardous Substances Data)

Usage

Structural Features

Contains a 2-azetidinone ring
Includes a phenyl group
Incorporates an organosilicon compound with three isopropyl groups

Stereochemistry

(3R,4S) configuration

Chirality

Exhibits chirality, meaning it has a specific arrangement of atoms that gives it a non-superimposable mirror image

Potential Applications

Pharmaceuticals
Materials science
Synthetic intermediate for other compounds

Unique Properties

Chiral nature enhances its potential for selective interactions in biological systems
The presence of the phenyl group and the organosilicon moiety may impart specific chemical and physical properties conducive to various applications

Importance

Offers opportunities for the development of novel drugs or materials
Provides a versatile building block for organic synthesis due to its distinct structure and reactivity.

Upstream product

• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 132127-27-6 (1R,2S)-2-phenyl-1-cyclohexyl<(triisopropylsilyl)oxy>acetate 
• 132201-30-0 (+)-(1S,2R)-2-Phenyl-1-cyclohexyl triisopropylsilyloxyacetate 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 
• 132127-27-6 Triisopropylsilanyloxy-acetic acid (1R,2S)-2-phenyl-cyclohexyl ester 
• 144465-78-1 1-(4-Methoxyphenyl)-3-triisopropylsilyloxy-4-phenyl-2-azetidinone 
• 880781-87-3 3-pentyl triisopropylsilyloxyacetate 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 100-52-7 benzaldehyde 
• 13154-24-0 triisopropylsilyl chloride 
• 146924-94-9 (3R,4S)-(+)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 186613-02-5 cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one 
• 194234-97-4 3-Hydroxy-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 94612-33-6 1-(4-methoxyphenyl)-4-phenylazetidine-2,3-dione 

Downstream Products

• 289713-98-0 (3R,4S)-2-Oxo-4-phenyl-3-triisopropylsilanyloxy-azetidine-1-carboxylic acid benzyl ester 
• 618886-96-7 (3R,4S)-1-(3-iodobenzoyl)-3-triisopropylsilyloxy-4-phenylazetidin-2-one 
• 172213-23-9 (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-phenylazetidin-2-one 
• 155371-59-8 (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-phenylazetidin-2-one 
• 618887-00-6 (3R,4S)-1-(3-ethenylbenzoyl)-4-phenylazetidin-2-one 
• 618886-93-4 (3R,4S)-1-(3-ethenylbenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one 
• 618886-97-8 (3R,4S)-1-(3-ethenylbenzoyl)-3-triisopropylsilyloxy-4-phenylazetidin-2-one 
• 618887-04-0 2-debenzoyl-2-(3-iodobenzoyl)-3'N-debenzoyl-3'N-(3-ethenylbenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel 
• 133524-70-6 13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III 
• 125354-16-7 10-acetyldocetaxel 
• 173101-56-9 C₄₈H₅₃NO₁₄ 
• 300833-62-9 2-debenzoyl-2-(3,3-dimethylpent-4-enoyl)paclitaxel 
• 618428-01-6 2-debenzoyl-2-cinnamoylpaclitaxel 

Relevant articles and documents

Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-phenylisoserine, and Its Analogues via Chiral 3-Hydroxy-4-aryl-β-lactams through Chiral Ester Enolate-Imine Cyclocondensation

A highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with >96percent ee is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogues.

Ni-Catalyzed asymmetric reduction of α-keto-β-lactams: via DKR enabled by proton shuttling

Chiral α-hydroxy-β-lactams are key fragments of many bioactive compounds and antibiotics, and the development of efficient synthetic methods for these compounds is of great value. The highly enantioselective dynamic kinetic resolution (DKR) of α-keto-β-lactams was realized via a novel proton shuttling strategy. A wide range of α-keto-β-lactams were reduced efficiently and enantioselectively by Ni-catalyzed asymmetric hydrogenation, providing the corresponding α-hydroxy-β-lactam derivatives with high yields and enantioselectivities (up to 92% yield, up to 94% ee). Deuterium-labelling experiments indicate that phenylphosphinic acid plays a pivotal role in the DKR of α-keto-β-lactams by promoting the enolization process. The synthetic potential of this protocol was demonstrated by its application in the synthesis of a key intermediate of Taxol and (+)-epi-Cytoxazone. This journal is

Asymmetric mannich-type addition of lithium glycolates to imines producing 3-hydroxy-4-phenylazetidin-2-ones

The external chiral ligand-controlled asymmetric Mannich-type reaction of a binary-or ternary-complexed lithium ester enolate of protected glycolates with benzaldehyde imines gave the corresponding 3-trialkylsilyl-oxy-4-phenylazetidin-2-ones, applicable a

Structure-activity relationship study of taxoids for their ability to activate murine macrophages as well as inhibit the growth of macrophage-like cells

A series of new taxoids modified at the C-3′, C-3′N, C-10, C-2 and C-7 positions has been designed, synthesized and evaluated for their potency to induce NO and TNF production by peritoneal murine macrophages (Mφ) from LPS-responsive C3H/HeN and LPS-hyporesponsive C3H/HeJ strains and human blood cells, and for their ability to inhibit the growth of Mφ-like cell lines J774.1 and J7.DEF3. The SAR-study has shown that the nature of the substituents at these positions have critical effect on the induction of TNF and NO production by Mφ. Positions C-3′ and C-10 are the most flexible and an intriguing effect of the length of the substituents at the C-10 position is observed for taxoids bearing a straight chain alkanoyl moiety. An aromatic group at the C-3′N and C-2 positions is required for the activity, while only hydroxyl or acetyl substituents seem to be tolerated at the C-7 position. The natural stereochemistry in the C-13 isoserine side chain of the taxoids is an absolute requirement for macrophage activation. It has also been clearly shown that there is no correlation between the ability of the taxoids to induce TNF/NO production in C3H/HeN Mφ and the cytotoxicity against Mφ-like cells.

Borneol derivatives, methods of manufacturing them, and their pharmaceutical use

PCT No. PCT/DE96/00297 Sec. 371 Date Aug. 28, 1998 Sec. 102(e) Date Aug. 28, 1998 PCT Filed Feb. 19, 1996 PCT Pub. No. WO96/25392 PCT Pub. Date Aug. 22, 1996Borneol derivatives of formula I in which R1 to R5 and X1 to X2 are defined in the specification, and the method of making the same.

Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment

The present invention is directed to novel taxanes useful as chemotherapeutic agents or their precursors. Processes for preparing the novel taxanes include coupling reactions, in the presence of a base, of baccatin of formula (III) or (IV) STR1 with β-lac

Borenol derivatives, process for their production and their pharmaceutical use

The invention relates to borneol derivatives of general formula I STR1 in which R1 means C(O)--CH(OR6)--CH(NHR7)--R8, R2 means hydrogen, --OH, C1 -C10 alkyl, C1 -C10 alkoxy, --OC(O)R9a, --OSO2 R9a, --OP(O)(OH)2, NHR9a, NR9a R9b, R3 means hydrogen, --OH, C1 -C10 alkoxy, --OC(O)R9b, --OSO2 R9b, --OP(O)(OH)2, or R2, R3 together mean an oxygen atom, R4 means hydrogen, C1 -C10 alkyl, --(CH2)n --OR11a, R5 means hydrogen, C1 -C10 alkyl, --(CH2)p --OR11b, or R4, R5 together mean an oxygen atom, a=CHR10 group, n means 0 to 8, p means 1 to 8, R7 means --C(O)R12, --SO2 R12, --C(O)OR12, --C(O)NHR9d, --C(O)NR9d R9e, STR2 R8 means aryl, R9a-e, R12 are the same or different and mean C1 -C10 alkyl, C4 -C8 cycloalkyl, aryl, C7 -C16 aralkyl, R10 means hydrogen, C1 -C10 alkyl, --(CH2)s --OR14, s means 1 to 8, R6, R11a,b, R14 are the same or different and mean hydrogen, C1 -C10 alkyl, aryl, C7 -C16 aralkyl, --SO2 R9c, --P(O)(OH)2, R13, R15a,b are the same or different and mean hydrogen, C1 -C10 alkyl, aryl, C7 -C16 aralkyl, X1, X2 are the same or different and mean X, X can be hydrogen, halogen, --OH, --NO2, --N3, --CN, --NR15a R15b, --NHSO2 R15a, --CO2 R15, C1 -C10 alkyl, C1 -C10 alkoxy, C1 -C10 acyloxy, C1 -C10 acyl, and, if R15 means hydrogen, their salts with physiologically compatible bases, as well as the α-, β-or γ-cyclodextrin clathrates, as well as the compounds of formula I that are encapsulated with liposomes.

Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment

The present invention is directed to novel taxanes useful as chemotherapeutic agents or their precursors. Processes for preparing the novel taxanes include coupling reactions, in the presence of a base, of baccatin of formula (III) or (IV) STR1 with β-lac

New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method

Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-β-lactam is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10-deacetyl-7,10-bis(Troc)-taxol in good yields. Fully assigned 1H, 13C, and 2D (COSY and HETCOR) NMR spectra of taxol thus synthesized are shown and discussed.

New and efficient routes to norstatine and its analogs with high enantiomeric purity by β-Lactam Synthon Method

Norstatine and its analogs, i.e., 3-amino-2-hydroxyalkanoic acids, with high enantiomeric purity are obtained through effecient asymmetric synthesis of 3-silyloxy-β-lactams by chiral enolate - imine cyclocondensation, followed by hydrolysis.