131968-76-8

Upstream product

• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 141685-06-5 S-2-pyridyl acetoxythioacetate 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 13831-31-7 Acetoxyacetyl chloride 
• 104-94-9 4-methoxy-aniline 
• 100-52-7 benzaldehyde 
• 40339-42-2 4-methoxy-N-[(1Z)-phenylmethylene]aniline 
• 13831-30-6 acetoxyacetic acid 

Downstream Products

• 133066-59-8 (±)-cis-3-acetyloxy-4-phenylazetidin-2-one 
• 158811-30-4 10-O-deacetyl larotaxel 
• 156294-36-9 7-deoxy-7β, 8β-methylene-10-O-acetyldocetaxel 
• 146924-91-6 (-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 146924-90-5 (+)-cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 101067-78-1 (+/-)-(3R,4S)-3-hydroxy-4-phenyl-N-(4-methoxyphenyl)azetidin-2-one 
• 1379469-49-4 (3S,4S)-1-(4-methoxyphenyl)-4-phenyl-3-(1H-pyrrol-1-yl)azetidin-2-one 
• 1379469-46-1 (3R,4S)-1-(4-methoxyphenyl)-4-phenyl-3-(1H-pyrrol-1-yl)azetidin-2-one 

Relevant academic research and scientific papers

Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aromatic imines

Cycloaddition of imines derived from polycyclic aromatic amines with acid chloride (or equivalent) in the presence of triethylamine at -78°C to room temperature unexpectedly produced trans-β-lactams. (C) 2000 Elsevier Science Ltd.

Stereoselective synthesis of-lactams under diverse conditions: Unprecedented Observations

ferent reaction conditions have been used for this study. It is important to note that the stereochemistry of the-lactam formation reaction depends on the conditions of the experiments, structures of the imines and acid chlorides, order of addition of the

Synthesis and biological evaluation of novel larotaxel analogues

Taxoids are a class of successful drugs and have been successfully used in chemotherapy for a variety of cancer types. However, despite the hope and promises that these taxoids have engendered, their utility is hampered by some clinic limitations. Extensive structure-activity relationship (SAR) studies of toxoids have been performed in many different laboratories. Whereas, SAR studies that based on the new-generation toxoid, larotaxel, have not been reported yet. In view of the advantages in preclinical and clinical data of larotaxel over former toxoids, new taxoids that strategicly modified at the C3’/C3′-N and C2 positions of larotaxel were designed, semi-synthesized, and examined for their potency and efficacy in vitro. As a result, it has been shown that the majority of these larotaxel analogues are exceptionally potent against both drug-sensitive tumor cells and tumor cells with drug resistance arising from P-glycoprotein over expression. Further in vivo antitumor efficacies investigations revealed A2 might be a potent antitumor drug candidate for further preclinical evaluation.

Microwave-induced cycloaddition of imines with acid chlorides in absence of a tertiary amine: Unprecedented synthesis of β-lactams in dimethylformamide

Synthesis β-lactams in N,N-dimethylformamide proceeds through cycloaddition of acid chlorides with imines in a domestic microwave oven in the absence of a tertiary base. This is an unprecedented observation.

Paclitaxel Biosynthesis: Adenylation and Thiolation Domains of an NRPS TycA PheAT Module Produce Various Arylisoserine CoA Thioesters

Structure-activity relationship studies show that the phenylisoserinyl moiety of paclitaxel (Taxol) is largely necessary for the effective anticancer activity. Several paclitaxel analogues with a variant isoserinyl side chain have improved pharmaceutical

A mild and selective reduction of β-lactams: Rh-catalyzed hydrosilylation towards important pharmacological building blocks

Four-membered N-heterocyclic compounds exhibit a broad range of pharmacological activities. Herein, we report a useful rhodium-catalyzed protocol for the activation of phenylsilane to reduce tertiary β-lactams. Reaction with the tertiary amides was select

Stereospecific novel glycosylation of hydroxy β-lactams via iodine-catalyzed reaction: A new method for optical resolution

Glycosylation of racemic and optically active α-hydroxy β-lactams by reaction with a few glycal derivatives in the presence of catalytic amounts of iodine has provided stereospecific formation of α-glycosides. This method has been extended for the prepara

A new enzymatic strategy for the preparation of (2R,3S)-3-phenylisoserine: a key intermediate for the Taxol side chain

Burkholderia cepacia lipase PS-IM catalysed the hydrolysis of racemic ethyl 3-amino-3-phenyl-2-hydroxypropionate with excellent enantioselectivity (E >200), when the reaction was performed with added H2O as a nucleophile, in iPr2O, at 50 °C. The hydrolysis of the less reactive enantiomeric ethyl 3-amino-3-phenyl-2-hydroxypropionate with 18% HCl afforded the corresponding enantiomerically pure (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid hydrochloride, a key intermediate for the Taxol side chain.

Arthrobacter sp.: a lipase of choice for the kinetic resolution of racemic arylazetidinone precursors of taxanoid side chains

The native strain of Arthrobacter sp. (MTCC 5125) bearing a lipase has been found to be the most effective in the kinetic resolution of racemic arylazetidinones for producing cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone, cis-(3R,4S)-3-

Reductive ring opening of 2-azetidinones promoted by sodium borohydride

Variously substituted 2-azetidinones 3 and 4 were reacted with sodium borohydride in aqueous isopropanol giving 3-aminopropan-1,2-dioles 5 and 7. Reaction extent was dependent upon the substitution pattern in the 3- and 4-positions of the 2-azetidinone ri