148968-08-5

Upstream product

• 19810-31-2 Benzyloxyacetyl chloride 
• 24978-42-5 1,4-bis(4'-methoxyphenyl)-1,4-diazabuta-1,3-diene 
• 130422-40-1 cis-1-p-methoxyphenyl-3-benzyloxy-4-styrylazetidin-2-one 
• 24978-42-5 (E,E)-N¹,N²-bis(4-methoxyphenyl)ethane-1,2-diimine 
• 104-94-9 4-methoxy-aniline 
• 88315-63-3 (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline 
• 153545-43-8 (4S,5S,3'R,4'S,3''S,4''R)-2,2-Dimethyl-4,5-bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>-1,3-dioxolane 
• 153472-20-9 C₂₁H₂₄N₂O₄ 
• 153545-44-9 (1S,2S,3'R,4'S,3''S,4''R)-1,2-Bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>ethane-1,2-diol 
• 141268-44-2 1-(4-methoxyphenyl)-3-(phenylmethoxy)-4-(1,4-dioxaspiro<4.5>dec-2-yl)azetidin-2-one 
• 141781-23-9 [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine 
• 139007-45-7 S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate 
• 153472-25-4 C₃₉H₄₀N₂O₈ 
• 148903-76-8 (3R,4S,4'S,5'S) N-(p-anisyl)-3-benzyloxy-4-azetidin-2-one 

Downstream Products

• 183184-66-9 (+)-(3R,4S)-3-benzyloxy-1-(4-methoxyphenyl)-4-{[(4-methoxyphenyl)imino]methyl}azetidin-2-one 
• 183066-56-0 (3R,4S)-4-[(E)-Benzylimino-methyl]-3-benzyloxy-1-(4-methoxy-phenyl)-azetidin-2-one 
• 160334-80-5 (-)-(3R,4S)-trans-3-benzyloxy-4-formyl-1-(p-methoxyphenyl)-2-azetidinone 
• 663619-26-9 (3R,4S)-3-Benzyloxy-4-((R)-1-hydroxy-3-phenyl-prop-2-ynyl)-1-(4-methoxy-phenyl)-azetidin-2-one 
• 892397-24-9 (3R,4S)-3-benzyloxy-4-(hept-1-enyl)-1-(4-methoxyphenyl)azetidin-2-one 
• 153463-33-3 (4S)-4-<1(R)-<(tert-Butyldimethylsilyl)oxy>benzyl>-1-(4-methoxyphenyl)azetidine-2,3-dione 
• 153463-35-5 (3R,4S)-4-<1(R)-<(tert-Butyldimethylsilyl)oxy>benzyl>-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one 
• 159612-41-6 Methyl (2S,3R)-3-<(tert-butyldimethylsilyl)oxy>-2-<(4-methoxyphenyl)amino>-3-phenylpropanoate 
• 159612-40-5 (S)-4-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-(4-methoxy-phenyl)-oxazolidine-2,5-dione 
• 159612-39-2 (3R,4S)-3-(Benzyloxy)-4-<(R)-1-<(tert-butyldimethylsilyl)oxy>benzyl>-1-(4-methoxyphenyl)azetidin-2-one 
• 865357-67-1 C₁₈H₁₇NO₄ 

Relevant academic research and scientific papers

Optically active 4-formyl β-lactams: Microwave-induced deacetonation-oxidation

Microwave-induced chiral synthesis of 4-formyl β-lactams is performed following a one-pot reaction. The deprotection of the ketal with aqueous bismuth nitrate and subsequent oxidation of the diol to aldehyde by aqueous sodium metaperiodate is accomplished

Stereocontrolled access to orthogonally protected anti,anti-4- aminopiperidine-3,5-diols through chemoselective reduction of enantiopure β-lactam cyanohydrins

(Chemical Equation Presented) The cyanosilylation of enantiopure 4-oxoazetidine-2-carbaldehydes with tert-butyldimethylsilyl cyanide was promoted by either molecular sieves or catalytic amount of sodium carbonate to give O-silylated β-lactam cyanohydrins

4-Formylazetidin-2-ones, synthon for the synthesis of (2R,3S) and (2S,3R)-3-amino-2-hydroxydecanoic acid (AHDA)

An efficient synthesis of 3-amino-2-hydroxydecanoic acid (AHDA), a nonproteinogenic amino acid, using enantiopure 3-benzyloxy-4-formylazetidin-2-one as a building block is described. Both the enantiomers of AHDA have been synthesized from the corresponding enantiomer of 3-benzyloxy-4-formylazetidin-2-one in good yield and optical purity.

Facile transformation of 3,4-disubstituted 2-azetidinones to chiral 5,6-dihydro-2-pyridones

Chiral 5,6-disubstituted-5,6-dihydro-2(1H)-pyridones were prepared efficiently from readily accessible 3,4-disubstituted-2-azetidinones having preadjusted substituents and stereochemistry through the reductive ring opening of 2-azetidinones followed by Z-selective installation of acetate moiety and re-cyclization to 2-pyridones.

Base-promoted isomerization of cis-4-formyl-2-azetidinones: Chemoselective C4-epimerization vs rearrangement to cyclic enaminones

Two simple, efficient, and complementary methods for the regiospecific C4-epimerization of cis-4-formyl-2-azetidinones 1-3 are described. The first method uses 40% aqueous dimethylamine as reagent in heterogeneous medium with benzene at room temperature, in the presence of benzyltributylammonium bromide (3-4 mol %) as the phase-transfer catalyst. This transformation tolerates alkyl, alkenyl, alkynyl, aryl, and alkoxy substituents at the C3 of the 2-azetidinone ring. However, limitations of this isomerization are as follows: (i) only N-(p-methoxyphenyl)-β-lactams can be used, and (ii) transformation is less compatible with heteroatomic substituents bonded to the C3 position of the 2-azetidinone ring. A highly general solution to these problems relies on the use of sodium carbonate as the isomerization reagent in different solvents. We also describe a novel base-promoted rearrangement of the β-lactam ring to cyclic enaminones 6 and 21, involving an E1cB-elimination reaction in cis-4-formyl-2-azetidinones.

Synthesis of novel 4-(5'-pyrrolidinyl)-β-lactams

The synthesis of novel 4-(5'-pyrrolidinyl)-β-lactams from imines derived from 4-formyl-β-lactams and α-amino esters via cascade imine → azomethine ylide → 1,3-dipolar cycloaddition reactions is described. These cascades are endo-specific, exhibit facial stereoselectivity and occur in good to excellent yields.

C4,C4'-bis-β-lactam to fused bis-γ-lactam rearrangement

Optically pure cis,cis-C4,C4'-bis-β-lactams 1a-d are obtained in good to excellent yields, in a single step, following two different approaches. Staudinger reaction of (S)-(4-phenyl-2-oxooxazolidinyl)acetyl chloride (2a) and p-anisyldiimine gave the corresponding bis-β-lactam 1a as a single enantiomer. The reaction of glyoxal diimine derived from (S)-α-phenylethylamine and different alkoxy-substituted acid chlorides gave diastereomeric mixtures of cis,cis-bis-β-lactams 1b-d, enantiomers at the bicyclic skeleton. The configuration of all compounds has been determined by X-ray diffraction analysis of enantiomerically pure aldehyde 4a and bis-β-lactam 1b-α. The remaining bicyclic lactams have been chemically correlated to compound 1b-α and their configurations assigned. Starting from enantiomerically pure 4-formyl-2-azetidinone 4b, sequential imine formation and ketene cycloaddition allowed the synthesis of differently substituted, optically pure cis,cis-C4,C4'-bis-β-lactams 1f-i in good overall yields. C4,C4'-Bis-β-lactams smoothly rearranged to fused trans,trans-bis-γ-lactams 7 upon basic treatment (NaOMe/MeOH) in a totally stereoselective process. The presence of alkyl groups attached to the lactam nitrogen inhibits the rearrangement. Differently substituted (aryl and alkyl substituents in either rings) bicyclic β-lactam systems gave the selective opening of the ring with the aromatic substituent attached to the lactam nitrogen. Monocyclic 2-azetidinones 8 with an amino ester side chain at C4 are then obtained. The synthesis of trans,cis-C4,C4'-bis-β-lactam 1j and trans,trans-C4,C4'-bis-β-lactam 1l has also been effected in the racemic form. Compound 1j with a trans,cis stereochemistry rearranged to cis,trans-bis-γ-lactam 7d in the presence of base while the trans,trans-bicycle 1l gave monocyclic 2-azetidinone 8c with an amino ester side chain. Finally, trans,trans-bis-γ-lactam 1l can be synthesized in a single step from glyoxal diimine 3a employing an excess of lithium isovalerate. A reaction pathway to account for all the observed data is proposed.

Application of (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol in the formal total synthesis of carbapenems, novel 4-cyano-β-lactams and β-hydroxy aspartates

The imines derived from (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol furnished cis-β-lactams stereoselectively on the Staudinger reaction. These homochiral cis-β-lactams were converted in to cis-β-lactams possessing aminol side chain at C-4. These aminols

Synthesis and Biological Evaluation of C-3'-Modified Analogs of 9(R)-Dihydrotaxol

Taxol (1) is considered a most exciting new drug in cancer chemotherapy.The promising antitumor activity of 9(R)-dihydrotaxol (3) encouraged us to further explore the structure-activity relationship of this new member of the taxane family.Studies indicate