149198-47-0

Basic information

• Product Name: (3R,4S)-tert-Butyl 2-oxo-4-phenyl-3-(triethylsilyloxy)azetidine-1-carboxylate
• Synonyms: DOCETAXEL SIDE CHAIN NO 2;(3R,4S)-TERT-BUTYL 2-OXO-4-PHENYL-3-(TRIETHYLSILYLOXY)AZETIDINE-1-CARBOXYLATE;(3R,4S)-2-Oxo-4-phenyl-3-[(triethylsilyl)oxy]-1-azetidinecarboxylic acid 1,1-dimethylethyl ester;(3r,4s)-1-Azetidine Carboxylic Acid-2-Oxo-4-Phenyl-3-[(Triethylsilyl)Oxy]-1,1-Dimethyl Ethyl Ester;(3R,4S)-1-AZETIDINECARBOXYLIC ACID 2-OXO-4-PHENYL-3-[(TRIETHYLSILY)OXY]-1,1-DIMETHYLETHYL ESTER;(3R,4S)-1-Azetidinecarboxylicacid-2-Oxo-4-Phenyl-3-[(Triethylsily)Oxy]-1,1-DimethylethylEsterCasNo.;(3R,4S)-1-TERT-BUTOXYCARBONYL-3-TRIETHYLSILYLOXY-4-PHENYL-2-AZETIDINONE;(3R,4S)-1-Azetidinecarboxylic
• CAS NO: 149198-47-0
• Molecular Formula: C₂₀H₃₁NO₄Si
• Molecular Weight: 377.55
• Product Categories: CHIRAL CHEMICALS;Intermediates;Ketone;Chiral Reagents;Heterocycles
• Mol File: 149198-47-0.mol

Chemical Properties

• Boiling Point: 463.1 °C at 760 mmHg
• Flash Point: 233.9 °C
• Appearance: /
• Density: 1.07
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -4.79±0.60(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: (3R,4S)-tert-Butyl 2-oxo-4-phenyl-3-(triethylsilyloxy)azetidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-tert-Butyl 2-oxo-4-phenyl-3-(triethylsilyloxy)azetidine-1-carboxylate(149198-47-0)
• EPA Substance Registry System: (3R,4S)-tert-Butyl 2-oxo-4-phenyl-3-(triethylsilyloxy)azetidine-1-carboxylate(149198-47-0)

Safety Data

• Hazardous Substances Data: 149198-47-0(Hazardous Substances Data)

Usage

Chemical Properties

Syrup

InChI:InChI=1/C20H31NO4Si/c1-7-26(8-2,9-3)25-17-16(15-13-11-10-12-14-15)21(18(17)22)19(23)24-20(4,5)6/h10-14,16-17H,7-9H2,1-6H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 149140-54-5 (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one 
• 994-30-9 triethylsilyl chloride 
• 132127-34-5 (3R,4S)-3-hydroxy-4-phenylazetidin-2-one 
• 132127-31-2 (3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one 
• 288-32-4 1H-imidazole 
• 17922-24-6 tert-butyloxydiphenylsilyl chloride 
• 39994-75-7 L-threonine methyl ester hydrochloride 

Downstream Products

• 179065-16-8 C₅₃H₇₀Cl₃NO₁₆Si 
• 181419-96-5 1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-10-deacetyl-7-O-triethylsilylbaccatin III 
• 181421-13-6 1-O-allyl-13-O-[(2R,3S)-3-(tert-butoxycarbonylamino)-3-phenyl-2-(triethylsilyloxy)propionyl]-4,10-dideacetyl-4-O-propionyl-7-O-triethylsilylbaccatin III 
• 332345-19-4 C₅₀H₇₈N₄O₁₃Si₂ 
• 325735-44-2 [2'R,3'S]-10-allyl-13-O-(3-tert-butoxycarbonylamino-2-O-triethylsilyl-3-phenylisoserinyl)-10-deacetoxy-7-O-triethylsilylbaccatin III 
• 162785-14-0 C₄₇H₅₉NO₁₅S 
• 159212-06-3 (2'R,3'S)-2',7,10-tris-O-(triethylsilyl)-2-desbenzoyl-2-(4-chlorobenzoyl)-10-deacetyl-N-desbenzoyl-N-(t-butoxycarbonyl)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.

The discovery of BMS-275183: An orally efficacious novel taxane

The evolution of 2, a C-4-methylcarbonate analogue of paclitaxel with minimal oral bioavailability and oral efficacy, into its C-3′ -t-butyl-3′-N-t-butyloxycarbonyl analogue (15i), a novel taxane with oral efficacy in preclinical models that is comparable to iv administered paclitaxel, is described.

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.

10-desacetoxytaxol derivatives

The present invention relates to 10-desacetoxytaxol and derivatives thereof, which are useful as antitumor agents. These compounds have the formula STR1 wherein R2 is hydrogen, hydroxy or a protected hydroxy group; R3 and R4 are independently hydrogen, hydroxy, a protected hydroxy group, methyl, --SH, --NH2, or --NR8 R9 ; R5 is R10, or --OR10 ; R6 and R7 are independently hydrogen, alkyl, or aryl; R8 and R9 are independently hydrogen, alkyl, alkenyl, alkynyl, or aryl; and R10 is alkoxy, alkyl, alkenyl, alkynl, or aryl.

7,8-cyclopropataxanes

An antitumor compound of formula I STR1 in which R1 is --CORz in which Rz is t-butyloxy, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, or phenyl, optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or --CF3 groups; R2 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, furyl, thienyl or phenyl, and furthermore Rx can be optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or --CF3 groups; R3 is OCOR, --OCOOR, H, or OH; R4 is hydrogen; or R3 and R4 jointly form a carbonyl group; and R is C1-6 alkyl. Also provided by this invention are pharmaceutical formulations (compositions) and a method of treating mammalian tumors with a compound of formula I.

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.

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.