Synthesis of 2-amino-2-deoxy-D-talose and 2-amino-2-deoxy-D-galactose

1968 ◽  
Vol 46 (15) ◽  
pp. 2481-2484 ◽  
Author(s):  
M. B. Perry ◽  
Ann C. Webb
Keyword(s):  
Hydrochloric Acid ◽  
Sodium Methoxide ◽  
Ammonia Solution ◽  
Nef Reaction ◽  
Derivatives Of ◽  
Methanolic Ammonia

Treatment of D-lyxose with nitromethane in the presence of sodium methoxide gave 1-deoxy-1-nitro-D-galactitol which, after conversion to 2,3,4,5,6-penta-O-acetyl-1-deoxy-1-nitro-D-galactitol, reacted with saturated methanolic ammonia solution to yield 2-acetamido-1,2-dideoxy-1-nitro-D-talitol and 2-acetamido-1,2-dideoxy-1-nitro-D-galactitol. 2-Acetamido-1,2-dideoxy-1-nitro-D-talitol and 2-acetamido-1,2-dideoxy-1-nitro-D-galactitol were converted by a modified Nef reaction to 2-acetamido-2-deoxy-D-talose and 2-acetamido-2-deoxy-D-galactose which on hydrolysis with hydrochloric acid afforded 2-amino-2-deoxy-D-talose hydrochloride and 2-amino-2-deoxy-D-galactose hydrochloride. The properties and derivatives of the aminoglycoses are described.

Synthetic use of the ribosyl derivatives of 2,4- and 2,5-thiazolidinediones

1979 ◽  
Vol 44 (5) ◽  
pp. 1475-1482 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Zdeněk Točík ◽  
Jiří Beránek
Keyword(s):  
Hydrazine Hydrate ◽  
Hydrogen Chloride ◽  
Sodium Methoxide ◽  
Aqueous Ammonia ◽  
Hydroxylamine Hydrochloride ◽  
Acetyl Derivative ◽  
High Yield ◽  
Derivatives Of ◽  
Methanolic Ammonia

On ribosidation of 2,4-thiazolidinedione (2,5-thiazolidinedione, respectively), the 3-β-D-ribofuranosyl derivative is formed in high yield, either the benzoyl derivative Ia (IIa) or the acetyl derivative Ib (IIb). The unsubstituted ribosyl derivative Ic is formed from the acetyl derivative Ib by methanolic hydrogen chloride. The benzoylated ribosyl-2,4-thiazolidinedione Ia affords the benzoylated ribosylurea III on reaction with aqueous ammonia, the hydroxyethylurea derivative IVa with 2-aminoethanol, the semicarbazide derivative Va with hydrazine hydrate, the ribosylhydroxyurea derivative VIa on reaction with hydroxylamine hydrochloride and triethylamine, the benzoyl derivative of ribosylbiuret VII with O-methylisourea hydrochloride and triethylamine, and (analogously) ribosylisothiobiuret VIII with S-methylisothiourea. Methanolysis of the benzoyl derivative of hydroxyethylurea IVa with sodium methoxide affords the unprotected riboside IVb. Ribosylhydroxyurea VIb is formed on debenzoylation of compound VIa with methanolic ammonia. Acetylation of compound VIb furnishes the pentaacetyl derivative VIc.

scholarly journals Synthesis of acylic derivatives of prolylleucylglycinamide

2019 ◽  
Vol 55 (4) ◽  
pp. 429-435
Author(s):  
V. A. Haidukevich ◽  
S. K. Petkevich ◽  
E. G. Karankevich ◽  
P. V. Kurman ◽  
Z. I. Kuvaeva ◽  
...  
Keyword(s):  
Formic Acid ◽  
Hydrogen Chloride ◽  
Carboxylic Acids ◽  
Ethyl Ester ◽  
Ammonia Solution ◽  
Dioxane Solution ◽  
Mixed Anhydride ◽  
Derivatives Of ◽  
Acyl Derivatives ◽  
Methanolic Ammonia

Tert-butyloxycarbonylprolylleucylglycinamide is obtained both by the interaction of tert-butyloxycarbonylprol ylleucylglycine ethyl ester with a methanolic ammonia solution and by the reaction of glycine amide with a mixed anhydride which was synthesized from tert-butyloxycarbonylprolylleucine and isobutylchloroformate. The removal of the tert-butyloxycarbonyl group by the action of formic acid or a dioxane solution of hydrogen chloride and treatment of the resulting salts with the corresponding base yielded a prolylleucylglycinamide, by the interaction of which with acetic, benzoic or 5-phenylisoxazole-3-carboxylic acids chlorides acyl derivatives of prolylleucylglycinamide are obtained.

Reactions of 3-cyano-1-methylquinolinium methyl sulphate with some C-acids and with p-nitroaniline

1981 ◽  
Vol 46 (2) ◽  
pp. 503-505 ◽  
Author(s):  
Oldřich Kocián ◽  
Miloslav Ferles
Keyword(s):  
Sodium Methoxide ◽  
Ethyl Cyanoacetate ◽  
Derivatives Of

The action of malononitrile, ethyl cyanoacetate, dibenzoylmethane and/or p-nitroaniline on compound I in the presence of sodium methoxide gives rise to derivatives of 3-cyano-1-methyl-1,4-dihydroquinoline, II and III

Preparation of Chloro and Sulfanyl Derivatives of 1-(2-Deoxy-4-C-hydroxymethyl-α-L-threo-Pentofuranosyl)uracil

1997 ◽  
Vol 62 (7) ◽  
pp. 1114-1127 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Jan Balzarini ◽  
Antonín Holý
Keyword(s):  
Nucleophilic Substitution ◽  
Hydrogen Chloride ◽  
Thionyl Chloride ◽  
Sodium Methoxide ◽  
Thioacetic Acid ◽  
Uracil Derivatives ◽  
Derivatives Of ◽  
Hiv 1

3'-Chloro and 3'-acetylsulfanyl derivatives of 1-(2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil were prepared by reaction of 2,3'-anhydro-1-{5'-O-benzoyl-4'-C-[(benzoyloxy)methyl]-2'-deoxy-α-L-erythro-pentofuranosyl}uracil (3) with hydrogen chloride and thioacetic acid, respectively. The reaction with hydrogen chloride gave a mixture of N-1 and N-3 substituted uracil derivatives 12 and 14. Reaction of 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-α-L-threo-pentofuranosyl}uracil (7) with thionyl chloride and subsequent debenzoylation afforded 1-(4-C-chloromethyl-2-deoxy-β-D-erythro-pentofuranosyl)uracil (19). Nucleophilic substitution with lithium thioacetate, followed by deacylation, converted 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (9) into 1-(2-deoxy-4-C-sulfanylmethyl-β-D-erythro-pentofuranosyl)uracil (21). The obtained thiols were oxidized with iodine or air to give 1,1'-[disulfandiylbis(2,3-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-3,1-diyl]di(pyrimidine-2,4-(1H,3H)-dione) (17) and 1,1'-[disulfandiylbis(2,5-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-5,1-diyl]di(pyrimidine-2,4(1H,3H)-dione) (22). Reaction of 1-{3-acetylsulfanyl-5-O-methanesulfonyl-4-C-[(benzoyloxy)methyl]-2,3-dideoxy-α-L-threo-pentofuranosyl)}uracil (24) with methanolic sodium methoxide afforded 1-(3,5-anhydro-2,3-dideoxy-4-C-hydroxymethyl-3-sulfanyl-α-L-threo-pentofuranosyl)uracil (25). The same reagent was used in the preparation of 1-(3,5-anhydro-2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil (26) from 1-{4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (8). From the series of 4'-substituted 2'-deoxyuridine derivatives, synthesized in this study, solely the 4'-chloromethyl derivative 19 and the oxetane derivative 26 exhibited an appreciable activity against HIV-1 and HIV-2.

A Synthesis of 2-Amino-2,6-dideoxy-D-(and L-)galaetose (Fucosamine) and 2-Amino-2,6-dideoxy-D-(and L-)talose (Pneumosamine)

1973 ◽  
Vol 51 (6) ◽  
pp. 974-977 ◽  
Author(s):  
Malcolm B. Perry ◽  
Virginia Daoust
Keyword(s):  
Similar Reaction ◽  
Reaction Sequence ◽  
Reaction Conditions ◽  
Nef Reaction ◽  
Methanolic Ammonia

5-Deoxy-D-lyxose underwent base-catalyzed addition with nitromethane to give a mixture of 1,6-dideoxy-1-nitro-D-galactitol and 1,6-dideoxy-1-nitro-D-talitol (ca. 2:1). Acetylation of the crystalline 1,6-dideoxy-1-nitro-D-galactitol gave 2,3,4,5-tetra-O-acetyl-1,6-dideoxy-1-nitro-D-galactitol which on treatment with methanolic ammonia afforded 2-acetamido-1,2,6-trideoxy-1-nitro-D-talitol and 2-acetamido-1,2,6-trideoxy-1-nitro-D-galactitol (ca. 3:1) which under the modified Nef reaction conditions gave 2-acetamido-2,6-dideoxy-D-talose and 2-acetamido-2,6-dideoxy-D-galactose respectively. The glycoses were converted to 2-amino-2,6-dideoxy-D-talose hydrochloride and 2-amino-2,6-dideoxy-D-galactose hydrochloride on hydrolysis with hydrochloric acid.A similar reaction sequence applied to 5-deoxy-L-lyxose afforded the L-enantiomorphic intermediates, and gave 2-amino-2,6-dideoxy-L-talose hydrochloride and 2-amino-2,6-dideoxy-L-galactose hydrochloride as final products.

scholarly journals Synthesis and anticonvulsant activity of 6-methyl-2-((2-oxo-2-arylethyl)thio)pyrimidin-4(3 H)-one derivatives and products of their cyclization

Pharmacia ◽  
2019 ◽  
Vol 66 (3) ◽  
pp. 141-146
Author(s):  
Hanna Severina ◽  
Olga O. Skupa ◽  
Natalya I. Voloshchuk ◽  
Marharyta M. Suleiman ◽  
Victoriya A. Georgiyants
Keyword(s):  
Sulphuric Acid ◽  
Anticonvulsant Activity ◽  
Sodium Methoxide ◽  
Structure Activity ◽  
Phenacyl Bromides ◽  
Pharmacological Screening ◽  
High Yields ◽  
Derivatives Of

The alkylation of 6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidine-4-one phenacyl bromides under different conditions was investigated. It was found that during the reaction in the medium of DMF/K2CO3 a mixture of 2-(2-aryl-2-oxoethyl)thio-6-methyl-pyrimidine-4(3H)-one and 3-hydroxy-3-aryl-7-methyl-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-5-one was formed. The holding of the resulting mixture in the concentrated sulphuric acid leads to the formation of cyclization products - derivatives of 3-aryl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one with high yields. Individual S-alkylated derivatives – 2-(2-aryl-2-oxoethyl)thio-6-methyl-pyrimidine-4(3H)-one - were obtained by reacting in methanol in the presence of sodium methoxide. Pharmacological screening of synthesized compounds for anticonvulsant activity on the model of pentylenetetrazole seizures in rats was carried out and some regularity “structure-activity” was established.

Alkaloids of the Australian Rutaceae: Melicope fareana. IV. Some Reactions of 1-Methyl-4-quinolone-3-carboxyic Acid, a Degradation Product of the Alkaloids

1949 ◽  
Vol 2 (2) ◽  
pp. 272 ◽  
Author(s):  
JR Price
Keyword(s):  
Nitric Acid ◽  
Carboxylic Acid ◽  
Hydrochloric Acid ◽  
Degradation Product ◽  
Carboxyl Groups ◽  
Methyl Groups ◽  
Derivatives Of

Melicopine, melicopidine, and melicopicine are each oxidized by nitric acid to the same acid, C11H9O3N. Decarboxylation gives 1-methyl-4-quinolone (I) and the acid is shown to be 1-methyl-4-quinolone-3-carboxylic acid (II). The 3- and 6- mononitro-, 3,6-dinitro-, and 2-hydroxy-3,6-dinitro- derivatives of 1-methyl-4-quinolone have been prepared and the orientation of the substituents established by oxidation of the hydroxydinitro- compound to 5-nitro-N-methylanthranilic acid. 1-Methy1-4-quinolone-3-carboxylic acid is readily converted to a tetrahydro- derivative. The carboxyl groups in II and in the tetrahydro- acid are reduced by zinc and hydrochloric acid to methyl groups.

O-Benzylidene Derivatives of D-Arabinose Diethyl and Dipropyl Dithioacetal

1996 ◽  
Vol 49 (3) ◽  
pp. 273 ◽  
Author(s):  
J Kuszmann ◽  
E Gacsbaitz
Keyword(s):  
Hydrochloric Acid ◽  
Zinc Chloride ◽  
Partial Hydrolysis ◽  
Kinetic Control ◽  
Toluenesulfonic Acid ◽  
Thermodynamic Phase ◽  
Hydrolysis Of ◽  
Derivatives Of

Benzylidenation of D-arabinose diethyl and dipropyl dithioacetals with α,α-dimethoxytoluene in the presence of p-toluenesulfonic acid has been studied in detail. Under kinetic control the two terminal dioxolan -type 4,5-O-(R)- and 4,5-O-(S)-benzylidene diastereomers are formed first which are in equilibrium with each other In the thermodynamic phase of the reaction the corresponding dioxan -type 3,5-O-(R)- benzylidene isomer is formed too, but all three monobenzylidene isomers are gradually converted into the four possible dioxolan -type 2,3 : 4,5-di-O benzylidene diastereomers . The dioxan -type 2,4:3,5-di-O-benzylidene isomer was present only in trace amounts. When benzaldehyde was used as reagent in the presence of hydrochloric acid or zinc chloride only the 2,3: 4,5-di-O-benzylidene diastereomers were formed. Partial hydrolysis of the dibenzylidene derivatives yielded the corresponding 2,3-O-benzylidene diastereomers. Structures, including the chirality of the benzylidene groups, were determined by n.m.r. spectroscopy. A mechanism suggested for the reaction was partially supported by equilibration studies.

General Method of Preparation of N-[(S)-(3-Hydroxy-2-phosphonomethoxypropyl)] Derivatives of Heterocyclic Bases

1993 ◽  
Vol 58 (5) ◽  
pp. 1151-1163 ◽  
Author(s):  
Petr Alexander ◽  
Antonín Holý
Keyword(s):  
Sodium Salt ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
Cesium Carbonate ◽  
Analogous Reaction ◽  
Sodium Salts ◽  
Heterocyclic Bases ◽  
Derivatives Of ◽  
General Method ◽  
Methanolic Ammonia

Reaction of (R)-1-O-p-toluenesulfonyl-1,2,3-propanetriol (IV) with N-trimethylacetylimidazole (II) afforded (R)-1-O-p-toluenesulfonyl-3-O-trimethyacetyl-1,2,3-propanetriol (V) which was reacted with dimethoxymethane in the presence of phosphorus pentoxide to give (R)-2-O-methoxymethyl-1-O-p-toluenesulfonyl-3-O-trimethyacetyl-1,2,3-propanetriol (VI). Compound VI was treated with acetic anhydride and boron trifluoride etherate and the obtained 2-acetoxy derivative VII reacted with bromotrimethylsilane to give the intermediary bromomethyl ether VIII. Compound VIII on reaction with tris(2-propyl) phosphite afforded (R)-2-O-bis(2-propyl)phosphonomethyl-1-O-p-toluenesulfonyl-3-O-trimethyacetyl-1,2,3-propanetriol (IX). Condensation of synthon IX with sodium salts of adenine, 2,6-diaminopurine, or with cytosine, 6-azacytosine or 2-chloroadenine in the presence of cesium carbonate, afforded fully protected diesters X and XIIIb which on methanolysis and reaction with bromotrimethylsilane gave N-[(S)-(3-hydroxy-2-phosphonomethoxypropyl)] derivatives of adenine (XIa), 2- chloroadenine (XIb), 2,6-diaminopurine (XIc), cytosine (XIVa) and 6-azacytosine (XIVb). In an analogous reaction, sodium salt of 4-methoxy-2-pyrimidone reacted with compound IX to give an intermediate XIIIa which on treatment with methanolic ammonia and subsequent deblocking under the same conditions also afforded the cytosine derivative XIVa. Sodium salt of 2-amino-6-chloropurine was in this way converted into the corresponding 2-aminopurine derivative XVIII. Deprotection of this compound gave 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)-2-aminopurine (XIX).

Extraction of zirconium and hafnium from hydrochloric acid solutions with derivatives of diantipyrylmethane

1975 ◽  
Vol 80 (2) ◽  
pp. 311-318
Author(s):  
A.I. Busev ◽  
V.P. Zhivopistsev ◽  
B.I. Petrov ◽  
M.I. Degtev ◽  
P. Nenning
Keyword(s):  
Hydrochloric Acid ◽  
Acid Solutions ◽  
Hydrochloric Acid Solutions ◽  
Derivatives Of
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