- Hydrogen Bond Donor Catalyzed Cationic Polymerization of Vinyl Ethers
-
The synthesis of high-molecular-weight poly(vinyl ethers) under mild conditions is a significant challenge, since cationic polymerization reactions are highly sensitive to chain-transfer and termination events. We identified a novel and highly effective h
- Kottisch, Veronika,Jermaks, Janis,Mak, Joe-Yee,Woltornist, Ryan A.,Lambert, Tristan H.,Fors, Brett P.
-
supporting information
p. 4535 - 4539
(2020/12/15)
-
- HCV POLYMERASE INHIBITORS
-
The invention provides compounds of the formula:(I) wherein B is a nucleobase selected from the groups (a) to (d) and the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.
- -
-
Page/Page column 65
(2015/03/28)
-
- DEUTERATED NUCLEOSIDE PRODRUGS USEFUL FOR TREATING HCV
-
Deuterated nucleoside analogs of Formula (I) and the pharmaceutically acceptable salts thereof are provided by this disclosure The variables, e.g., B1, Y, R1, R2, R3, R3′, R4, R5, R6, R7, R8, and R9 carry definitions set forth in the disclosure. Compounds of Formula (I) are deuterated at one or more positions and the deuterium enrichment at each deuterated positions is at least 50%. Compounds and salts of Formula (I) are useful for treating viral infections, including HCV infections.
- -
-
Paragraph 0297; 0298
(2014/10/29)
-
- Kinetics and mechanism of pyridinolyses of aryl methyl and aryl propyl chlorothiophosphates in acetonitrile
-
The nucleophilic substitution reactions of Y-aryl methyl (8) and Y-aryl propyl (10) chlorothiophosphates with X-pyridines are studied kinetically in acetonitrile at 35.0 °C. The Hammett and Broensted plots with X in the nucleophiles for both substrates ex
- Barai, Hasi Rani,Lee, Hai Whang
-
p. 483 - 488
(2014/03/21)
-
- METHODS OF PREPARING SUBSTITUTED NUCLEOTIDE ANALOGS
-
Disclosed herein are methods of preparing a phosphorothioate nucleotide analog, which are useful in treating diseases and/or conditions such as viral infections.
- -
-
Paragraph 0056
(2013/10/07)
-
- Thiophosphoramide-based cooperative catalysts for Bronsted acid promoted ionic diels-alder reactions
-
Three's a crowd: The combination of a Bronsted acid and a hydrogen-bond donor cocatalyst was found to promote various ionic [2+4] cycloadditions under mild reaction conditions (see scheme; Ts=4-toluenesulfonyl) . Thiophosphoramides are the most effective cocatalysts because of the stronger counterion activation effect resulting from three, rather than two, hydrogen bonds involved in anion binding.
- Borovika, Alina,Tang, Pui-In,Klapman, Seth,Nagorny, Pavel
-
supporting information
p. 13424 - 13428
(2014/01/06)
-
- Kinetics and mechanism of the aminolysis of aryl phenyl chlorothiophosphates with anilines
-
(Chemical Equation Presented) Kinetic studies of the reactions of aryl phenyl chlorothiophosphates (1) and aryl 4-chlorophenyl chlorothiophosphates (2) with substituted anilines in acetonitrile at 55.0°C are reported. The negative values of the cross-interaction constant ρXY (ρXY = -0.22 and -0.50 for 1 and 2, respectively) between substituents in the nucleophile (X) and substrate (Y) indicate that the reactions proceed by concerted SN2 mechanism. The primary kinetic isotope effects (kH/kD = 1.11-1.13 and 1.10-1.46 for 1 and 2, respectively) involving deuterated aniline nucleophiles are obtained. Front- and back-side nucleophilic attack on the substrates is proposed mainly on the basis of the primary kinetic isotope effects. A hydrogen-bonded, four-center-type transition state is suggested for a front-side attack, while the trigonal bipyramidal pentacoordinate transition state is suggested for a back-side attack. The MO theoretical calculations of the model reactions of dimethyl chlorothiophosphate (1′) and dimethyl chlorophosphate (3′) with ammonia are carried out. Considering the specific solvation effect, the front-side nucleophilic attack can occur competitively with the back-side attack in the reaction of 1′.
- Ul Hoque, Md. Ehtesham,Dey, Shuchismita,Guha, Arun Kanti,Chan, Kyung Kim,Lee, Bon-Su,Hai, Whang Lee
-
p. 5493 - 5499
(2008/02/09)
-
- Synthesis of novel chiral 2-Oxo- And 2-thio-1,3,2-oxazaphospholidines via asymmetric cyclization of L-methionol with (thio)phosphoryl dichlorides
-
In order to search for novel antitumor and antiviral agents with high activity and low toxicity, a series of chiral 2-thio(oxo)-1,3,2- oxazaphospholidines were synthesized via the reaction of L-methionol with all kinds of (thio)phosphoryl dichlorides in THF in the presence of triethylamine at room temperature. The structures of all of the new compounds were confirmed by elemental analyses, 1H, 31P NMR, and 1R spectra.
- Liu, Ling-Yan,Chen, Ru-Yu,Huang, You
-
-
- A comparative study of the hydrolysis pathways of substituted aryl phosphoramidate versus aryl thiophosphoramidate derivatives of stavudine
-
A comparative study of aryl phosphoramidate and aryl thiophosphoramidate derivatives of 2′,3′-didehydro-2′,3′-dideoxythymidine (d4T) was performed. The study focused on the nature of the substituents and the influence of a thiophosphoramidate in the structure of these derivatives. The rate of alkaline hydrolysis of these two types of d4T derivatives indicated that replacement of oxygen with sulfur decreases the rate of hydrolysis by twofold. Additionally, the activation energy (Ea) for the sulfur analogs is comparatively higher than that of the oxygen analogs. Notably, an intermediate was formed in the hydrolysis reaction of the sulfur analogs of d4T that was absent in the case of the oxygen analog, and the tentative structure of the intermediate was proposed based on LC/mass spectroscopy data. Using both HPLC and 31P-NMR techniques, we identified the hydrolysis product of the phosphoramidate derivatives and were able to show in in vitro studies that porcine liver esterase can hydrolyze the methyl ester portion of the phosphoramidate derivatives. Aryl phosphoramidate derivatives of d4T were 1000-fold more active than the corresponding aryl thiophosphoramidate derivatives, indicating that the energy of activation of hydrolysis of these phosphoramidate derivatives plays a significant role in their biological potency.
- Venkatachalam,Yu,Samuel,Qazi,Pendergrass,Uckun
-
p. 665 - 683
(2007/10/03)
-
- Phase-transfer catalysis (ptc) in organophosphorus compounds synthesis. 1: Liquid-liquid PTC synthesis of phosphorodichloridothioic acid O-aryl esters
-
Phase-transfer catalysis in the organophosphorus compounds synthesis reaches every day new limits. Our aim was to investigate the possibilities to apply this kind of catalysis to some organophosphorus compounds in different systems. Moreover, for the syst
- Dehelean, Gheorghe,Iliescu, Smaranda,Ilia, Gheorghe,Popa, Adriana,Macarie, Lavinia,Pǎcureanu, Liliana
-
p. 1293 - 1297
(2007/10/03)
-
- Synthesis of O,O,O-triaryl phosphorothioates and O-aryl phosphorodichloridothioates using poly(ethylene glycol) as a phase transfer catalyst
-
O,O,O-Triaryl phosphorothioates and O-aryl phosphorodichloridothioates have been prepared in good yields and purity from thiophosphoryl chloride and phenol using poly(ethylene glycol)-400 (PEG-400) as a phase transfer catalyst.
- Jadhav,Wadgaonkar,Salunkhe
-
p. 1473 - 1475
(2007/10/03)
-
- Phase-Transfer Reactions of Phosphorus Thiochloride with Phenols in the System Liquid-Solid Phase
-
Preparative syntheses of aryl phosphorodichloridothioates and 2-propynyl phosphorodichloridothioates via phase-transfer reactions of phosphorus thiochloride with phenols in the presence of solid bases were developed.
- Shipov,Genkina,Mastryukova,Kabachnik
-
p. 1345 - 1348
(2007/10/03)
-
- Studies on chiral thiophosphoric acids and their derivatives 16. - The asymmetric cyclization of L-(+)-prolinol with (thio)phosphoro(-no)dichloridates
-
The cyclizations of L-(+)-prolinol 5 with (thio)phosphoro(-no)dichloridates 6 give 1,2,3-azaphosphaoxabicyclo[3.3.0]octanes 7 consisting of unequal amounts of diastereoisomers, eight pairs of which have been successfully resolved by silica gel column chromatography or recrystallization. The influences of reaction temperature, solvent and substrate concentration upon the asymmetric induction have also been investigated.
- He, Zheng-Jie,Wang, You-Ming,Tang, Chu-Chi
-
-
- Studies on chiral thiophosphoric acids and their derivatives 14. The asymmetric cyclization of (+)-cis-1,2,2-trimethyl-1,3-diaminocyclopentane with thiophosphorodichloridates and o-(4-nitrophenyl)thiophosphorochloridates
-
The cyclization of (+)-cis-1,2,2-trimethyl-1,3-diaminocyclopentane 1 with thiophosphorodichloridates 2 or O-(4-nitrophenyl)thiophosphorochloridates 4 forms (+)-2,4,5-diazaphosphabicyclo[3.2.1]octane 3 and 3′, respectively, but the stereoselectivity arising from the condensation of (+)-1 with 4 is less than that of (+)-1 with 2. The distinction between the two product distributions might be due to the significance of different mechanistic routes. In the light of a trigonal bipyramid (TBP) intermediate and Berry pseudorotation (BPR) concept their mechanism are discussed.
- Tang, Chu-Chi,Lang, Hui-Fang,He, Zheng-Jie,Chen, Ru-Yu
-
p. 123 - 127
(2007/10/03)
-
- Thermal and spectral studies on cellulose arylthiophosphates in air
-
The thermal behaviour of cellulose and cellulose arylthiophosphate samples have been studied using DTA and TG techniques from ambient temperature to 600°C in static air atmosphere. First exotherm in DTA curves of cellulose arylthiophosphate samples caused
- Singh, Ranbir,Arora, Sanjiv,Lal, Krishan
-
-
- Synthesis and antimicrobial activity of 6-aryloxy/alkoxy-1,2,4,8,10,11-hexachloro-12H-dibenzodioxaphosphocin-6-sulfides
-
A series of 6-aryloxy/alkoxy-1,2,4,8,10,11-hexachloro-12H-dibenzo(1,3,2>dioxaphosphocin-6-sulfides (3) have been synthesized and their structures confirmed from elemental analyses and spectral (IR, 1H NMR and 31P NMR) data.The antimicrobial activity
- Raghu, K. V.,Reddy, B. Sankara,Reddy, C. Devendranath
-
p. 927 - 930
(2007/10/03)
-
- SYNTHESIS OF O-ARYL DICHLOROTHIOPHOSPHATES VIA PHASE-TRANSFER CATALYSIS
-
A convenient general method for synthesis of aryl dichlorothiophosphates via phase-transfer catalysis was developed.An influence of the reaction conditions on the yields and purity of the compounds synthesized was studied.
- Shipov, A. E.,Genkina, G. K.,Mastryukova, T. A.,Kabachnik, M. I.
-
p. 1196 - 1200
(2007/10/02)
-