132127-30-1

Basic information

• Product Name: (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one
• Synonyms: (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one
• CAS NO: 132127-30-1
• Molecular Weight: 277.439
• Mol File: 132127-30-1.mol

Chemical Properties

• CAS DataBase Reference: (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one(132127-30-1)
• EPA Substance Registry System: (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one(132127-30-1)

Safety Data

• Hazardous Substances Data: 132127-30-1(Hazardous Substances Data)

Upstream product

• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 132127-25-4 (1R,2S)-2-Phenyl-1-cyclohexyl t-butyldimethylsilyloxyacetate 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 950586-06-8 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-tert-butyldimethylsiloxy-3-(4-methoxyphenylamino)-3-phenylpropanoate 
• 950586-04-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-hydroxy-3-(4-methoxyphenylamino)-3-phenylpropanoate 
• 880781-88-4 (3R,4S)-3-tert-butyldimethylsiloxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 
• 132127-26-5 2-O-<<(tert-butyldimethylsilyl)oxy>acetyl>-10-(dicyclohexylsulfamoyl)-D-isoborneol 
• 132127-25-4 (tert-Butyl-dimethyl-silanyloxy)-acetic acid 2-phenyl-cyclohexyl ester 

Downstream Products

• 132127-34-5 (3R,4S)-3-hydroxy-4-phenylazetidin-2-one 
• 160237-83-2 7-(triethylsilyl)baccatin III 13--(2'R,3'S)-3'-phenylisoserinate> 
• 155399-27-2 7-(triethylsilyl)baccatin III 13- 
• 153695-19-3 N-(4-azidobenzoyl)-N-debenzoyltaxol 
• 133524-70-6 13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III 
• 160239-19-0 7-O-(triethylsilyl)baccatrin III 13-O-<(2R,3S)-N-benzoyl-2-O-(tert-butyldimethylsilyl)-3-cyclohexylisoserinate> 
• 160239-18-9 (3R,4S)-1-benzoyl-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-2-azetidinone 
• 186347-81-9 (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hexanoyl-4-phenyl-azetidin-2-one 
• 160239-17-8 (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-cyclohexyl-2-azetidinone 
• 155399-25-0 (3R,4S)-1-(benzyloxycarbonyl)-3-<(tert-butyldimethylsilyl)oxy>-4-phenyl-2-azetidinone 
• 152089-13-9 (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-oxo-4-phenyl-azetidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Asymmetric synthesis of 3-amino-2-hydroxyalkanoates by Mannich reaction of menthyl acetate with imines and subsequent oxidation

Lithium amide-assisted Mannich-type reaction of menthyl acetate-derived lithium enolate with PMP-arylaldimines and subsequent in situ oxidation with oxaziridine gave syn-3-amino-3-aryl-2-hydroxypropanoates with high syn-selectivity and diastereoselectivit

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.

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.