Synthesis and Properties of 5-Hydroxymethyl-2′-deoxyuridine and its α-Anomer

1971 ◽  
Vol 49 (5) ◽  
pp. 719-724 ◽  
Author(s):  
V. S. Gupta ◽  
G. L. Bubbar
Keyword(s):  
Absorption Spectra ◽  
Elemental Analysis ◽  
Mercuric Chloride ◽  
Room Temperature ◽  
Major Product ◽  
High Yield ◽  
Crystalline Solid ◽  
Fusion Method ◽  
Excellent Yield ◽  
High Yields

The synthesis and properties of 5-hydroxymethyldeoxyuridine (6) and its α-anomer 7 are described. Treatment of 5-hydroxymethyluracil (2) with trimethylchlorosilane in the presence of triethylamine gave 2,4,5-tris(trimethylsilyl)-5-oxymethyluracil (3) in excellent yield (92%) which, upon condensation with 3,5-di-(O-p-toluoyl)-2-deoxy-D-ribofuranosyl chloride in acetonitrile at room temperature, furnished an anomeric mixture of substituted nucleosides β-anomer (4) and α-anomer (5) in high yield 90% (by a fusion method (12) yield of blocked nucleosides was 70%). Compound 4 was the major product formed by both methods and was recovered as a crystalline solid in high yield. However, condensation of 3 with chlorosugar in benezene with mercuric chloride as a catalyst at room temperature gave a mixture of protected nucleosides; the amount of 5 formed was appreciably higher (34%) and was isolated as a microcrystalline solid from mother liquors in low yield (without the catalyst nucleosides were formed in low yield 30%). Removal of the blocking groups by alcoholysis gave 6 and 7 in high yields. The structure was confirmed by n.m.r. studies, u.v. and i.r. absorption spectra, elemental analysis, and by conversion of 4 to β-thymidine (8).

Reductions with sulfurated borohydrides. V. Reductions of ketones

1970 ◽  
Vol 48 (15) ◽  
pp. 2366-2371 ◽  
Author(s):  
J. M. Lalancette ◽  
A. Freche
Keyword(s):  
High Temperature ◽  
Carbonyl Group ◽  
Sodium Borohydride ◽  
Room Temperature ◽  
High Yield ◽  
High Yields ◽  
Very High

Ketones can be reduced with sulfurated sodium borohydride. Very high yield (≈90%) of the corresponding alcohol is obtained with the appropriate ratio of ketone and hydride at room temperature. The reaction is much influenced by the steric environment around the carbonyl group. At high temperature (65°) disulfides and tetrasulfides are produced. In some cases the structure of those sulfides have been established. Conjugated ketones can be reduced to the corresponding alcohols with very high yields.

scholarly journals Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline)

2018 ◽  
Vol 2018 ◽  
pp. 1-10
Author(s):  
Zegang Qiu ◽  
Kunjie Wang ◽  
Zhiqin Li ◽  
Tao Li ◽  
Jinhao Bai ◽  
...  
Keyword(s):  
Zinc Acetate ◽  
Dimethyl Carbonate ◽  
Reaction Pathway ◽  
Major Product ◽  
High Yield ◽  
Synthetic Route ◽  
Reaction Conditions ◽  
High Yields ◽  
By Products

The full N,N-methylation of 4,4′-methylenedianiline (MDA) with dimethyl carbonate (DMC) was investigated. The yield of the major product 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) reached as high as 97% over NaY catalyst at 190°C for 6 h. The catalyst could be used for two more times with acceptable MBDMA yields higher than 90%. The main by-products were identified as three N-methylated derivatives. Surprisingly, the formation of the N-methoxycarbonylation product was extremely restrained, which could be produced in high yields of 98% on zinc acetate catalyst. Furthermore, the reaction pathway to the major product MBDMA was proposed. Finally, a feasible synthetic route of 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) was established, featuring a high yield, mild reaction conditions, and simple operations.

Iodosulfonation of alkenes with benzenesulfinic acid – N-iodosuccinimide — Facile preparation of α,β-unsaturated sulfones

2006 ◽  
Vol 84 (4) ◽  
pp. 667-675 ◽  
Author(s):  
Russell R Wolff ◽  
Vikram Basava ◽  
Robert M Giuliano ◽  
Walter J Boyko ◽  
J Herman Schauble
Keyword(s):  
Room Temperature ◽  
High Yield ◽  
Allylic Alcohols ◽  
Neutral Alumina ◽  
Silyl Ethers ◽  
Step Procedure ◽  
Ferrier Rearrangement ◽  
Facile Preparation ◽  
High Yields ◽  
Yield And Purity

Reaction of alkenes and alkenols with N-iodosuccinimide (NIS) and benzenesulfinic acid in dichloromethane at room temperature affords vic-iodophenylsulfonyl adducts in good to high yields. Treatment of the iodosulfones with neutral alumina in dichloromethane at room temperature results in dehydroiodination to give the corresponding vinyl sulfones in high yield and purity by this convenient two-step procedure. Application of the iodosulfonation–dehydroiodination sequence to allylic alcohols and silyl ethers gave γ-oxygenated, α,β-unsaturated phenylsulfones, while the attempted iodosulfonation of glycals, as intermediates to vinyl sulfones, resulted in addition of benzenesulfinic acid with double bond shift (Ferrier rearrangement). Key words: iodosulfonation, vinyl sulfones, benzenesulfinic acid, N-iodosuccinimide, dehydroiodination.

scholarly journals The synthesis of esters of bilirubin

1973 ◽  
Vol 133 (3) ◽  
pp. 493-498 ◽  
Author(s):  
David W. Hutchinson ◽  
Brian Johnson ◽  
Alan J. Knell
Keyword(s):  
Mass Spectroscopy ◽  
Elemental Analysis ◽  
Room Temperature ◽  
Dimethyl Ester ◽  
Chloroform Solution ◽  
Methyl Ethyl ◽  
Benzyl Esters ◽  
High Yields

1-Alkyl-3-p-tolytriazenes were used to synthesize the methyl, ethyl, isopropyl and benzyl esters of bilirubin. Treatment of a chloroform solution of bilirubin with the triazene at room temperature gave high yields of the corresponding esters. These were identified by n.m.r. and mass spectroscopy together with elemental analysis. N.m.r. studies also suggest that bilirubin dimethyl ester is in the lactam rather than the lactim form.

Synthesis of 5-substituted ether derivatives of 5-hydroxymethyldeoxyuridine and their α-anomers

1970 ◽  
Vol 48 (20) ◽  
pp. 3147-3153 ◽  
Author(s):  
G. L. Bubbar ◽  
V. S. Gupta
Keyword(s):  
Absorption Spectra ◽  
Elemental Analysis ◽  
Thymidylate Synthetase ◽  
Crystalline Solids ◽  
Acid Catalyzed ◽  
High Yields ◽  
Derivatives Of

The synthesis and properties of ether derivatives 6a–d of 5-hydroxymethyldeoxyuridine and their corresponding α-anomers 7a–d are described. Acid-catalyzed etherification of 5-hydroxymethyluracil (1) gave the corresponding 5-alkoxymethyluracils 2a–e in excellent yields. Treatment of compounds 2a–e with trimethylchlorosilane gave bis(trimethylsilyl)pyrimidines 3a–e in high yields which, upon condensation with 3,5-di-(O-p-toluoyl)-2-deoxy-D-ribofuranosyl chloride, furnished an anomeric mixture of substituted nucleosides, β-anomers 4a–e and a-anomers 5(a–e). The nucleosides with β-configuration were the major products in each case and were recovered as crystalline solids in good yields. Deblocking of compounds 4a–d by alcoholysis resulted in the corresponding ether derivatives 6a–d. From mother liquors, two substituted α-anomers, 5a, b were isolated as crystalline solids in small yields. Compounds 7c, d were obtained from mother liquors after hydrolysis by using preparative t.l.c. The structures were confirmed on the basis of p.m.r. studies, u.v. and i.r. absorption spectra, and elemental analysis. The compounds 2a–e and 6a–d did not inhibit thymidylate synthetase at a concentration of 2.5 mM.

scholarly journals Iodination of industrially important aromatic compounds using N-iodosuccinimide by grinding method

2018 ◽  
Vol 7 (6) ◽  
pp. 477-486
Author(s):  
Vivek Sharma ◽  
Priyanka Srivastava ◽  
Santosh Kumar Bhardwaj ◽  
D.D. Agarwal
Keyword(s):  
Gas Chromatography ◽  
Reaction Time ◽  
Solid State ◽  
Aromatic Compounds ◽  
Room Temperature ◽  
High Yield ◽  
Short Reaction Time ◽  
Grinding Method ◽  
High Yields ◽  
Work Up

Abstract Iodination of various industrially and pharmaceutically important substituted aromatics has been achieved using N-iodosuccinimide (NIS) in solid state by grinding at room temperature. This method provides several advantages such as short reaction time (5–8 min), high yields (94–99%), and nonhazardous and simple work-up procedure. High gas chromatography (GC) purity (95–99.9%) suggests that the reaction is highly selective. Substrates which are sensitive to oxidation, viz aniline and phenols are iodinated smoothly in high yield.

Reaction behavior of the Collman reagent towards the nitrosyl carbonyls [CoNO(CO)3] and [Fe(NO)2(CO)2]

2017 ◽  
Vol 72 (6) ◽  
pp. 457-460
Author(s):  
Hans-Christian Böttcher ◽  
Wolfgang Beck
Keyword(s):  
Ir Spectra ◽  
Elemental Analysis ◽  
Room Temperature ◽  
Iron Carbonyl ◽  
Melting Points ◽  
Reaction Behavior ◽  
Formed Product ◽  
High Yields

AbstractReactions of the Collman reagent, Na2[Fe(CO)4]·1.5 dioxane, towards the nitrosyl carbonyls [CoNO(CO)3] and [Fe(NO)2(CO)2] in THF as the solvent at room temperature were investigated. Thereby a quick transfer of one nitrosyl ligand from the nitrosyl carbonyl molecule to the iron carbonyl metalate was observed. The reaction with the cobalt compound afforded in high yields the well-known species [Co(CO)4]− and [FeNO(CO)3]− isolated by addition of two equivalents of [PPN]+Cl− ([PPN]+= bis(triphenylphosphane)iminium cation) and characterized by their known IR spectra, by elemental analysis and their characteristic colors and melting points. In the reaction of the Collman reagent with [Fe(NO)2(CO)2] a clean transformation to the tricarbonylnitrosylferrate(1−) as the only formed product was observed.

Evaluation of germ plasm for resistant to Soybean mosaic virus (SMV)

2020 ◽  
Vol 21 (1) ◽  
pp. 6-9
Author(s):  
Wuye Ria Andayanie
Keyword(s):  
Abiotic Stress ◽  
Environmental Factors ◽  
Mosaic Virus ◽  
Polyclonal Antibody ◽  
Symptom Severity ◽  
Germ Plasm ◽  
Polyclonal Antibodies ◽  
Soybean Mosaic Virus ◽  
High Yield ◽  
High Yields

Soybean superior varieties with high yields and are resistant to abiotic stress have been largely released, although some varieties grown in the field are not resistant to SMV. In addition, the opportunity to obtain lines of hope as prospective varieties with high yield and resistance to SMV is very small. The method for evaluating soybean germplasm is based on serological observations of 98 accessions of leaf samples from SMV inoculation with T isolate. The evaluation results of 98 accessions based on visual observations showed 31 genotypes reacting very resistant or healthy to mild resistant category to SMV T isolate  with a percentage of symptom severity of 0 −30 %. Among 31 genotypes there are 2 genotypes (PI 200485; M8Grb 44; Mlg 3288) with the category of visually very resistant and resistant, respectively and  Mlg 3288  with the category of mild resistant.  They have a good agronomic appearance with a weight of 100 seeds (˃10 g) and react negatively with polyclonal antibodies to SMV, except Mlg 3288 reaction is not consistent, despite the weight of 100 seeds (˃ 10 g). Leaf samples from 98 accessions revealed various symptoms of SMV infection in the field. This diversity of symptoms is caused by susceptibility to accession, when infection occurs, and environmental factors. Keywords—: soybean; genotipe; Soybean mosaic virus (SMV); disease severity; polyclonal  antibody

scholarly journals Dichloro(η6-p-cymene)(P,P-diphenyl-N-propyl-phosphinous amide-κP)ruthenium(II)

Molbank ◽  
10.3390/m1217 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1217
Author(s):  
Rebeca González-Fernández ◽  
Pascale Crochet ◽  
Victorio Cadierno
Keyword(s):  
Ir Spectroscopy ◽  
Elemental Analysis ◽  
Title Compound ◽  
Room Temperature ◽  
Toluene Solution ◽  
Catalytic Behavior ◽  
Multinuclear Nmr

The title compound, i.e., [RuCl2(η6-p-cymene)(PPh2NHnPr)] (2), was obtained in a 71% yield by reacting a toluene solution of the chlorophosphine complex [RuCl2(η6-p-cymene)(PPh2Cl)] (1) with two equivalents of n-propylamine at room temperature. The aminophosphine complex 2 was characterized by elemental analysis, multinuclear NMR (31P{1H}, 1H and 13C{1H}) and IR spectroscopy. In addition, its catalytic behavior in the hydration of benzonitrile was briefly explored.

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