Detail of "3947-62-4"

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Letter: Synthesis of glycosides in which the aglycon is an N-(hydroxymethyl)amino-1,3,5-triazine derivative

Letter: Synthesis of glycosides in which the aglycon is an N-(hydroxymethyl)amino-1,3,5-triazine derivative. Bagga, Kishore; Dua, Geeta; Williams, Gerallt; Simmonds, Richard J. ( Institute of Biological Sciences, University of Wales, Aberystwyth SY23 3DD, UK). Glycoconjugate Journal, 14(4), 519-521 (English) 1997 Chapman & Hall. CODEN: GLJOEW.Several substances like 3947-62-4 may be metioned in this study. ISSN: 0282-0080. DOCUMENT TYPE: Journal CA Section: 33 (Carbohydrates) The synthesis of analogs of the anti-tumor drug 2-[N-(hydroxymethyl)methylamino]-4,6-bis(dimethylamino)-1,3,5-triazine (HMPMM) in which the OH or a dimethylamino group is replaced by a carbohydrate has been explored. Triazinyl b-glycosides were readily prepd. by reaction of sugars with trimethyl-triazinylammonium salts. These were made with one or two methylamino groups on the triazine for reaction with formaldehyde to give the cytotoxic NMeCH2OH group. However, reaction of the triazinyl glycosides with formaldehyde gave complex intractable mixts. When the carbohydrate portion was changed to the fully protected 2,3,4,6-tetra-O-acetyl glucose a good yield of the 2-[N-(hydroxymethyl)methylamino]-4-(dimethylamino)-1,3,5-triazin-2-yl tetra-O-acetyl b-glucoside was obtained. However, de-acetylation using sodium methoxide also removed the N-CH2OH group. We are investigating protection of the base-sensitive N-CH2OH group as trialkylsilyl and benzyl ethers and are looking at de-acetylation methods that are more selective. We have prepd. glycosides in which the sugar is joined through the oxygen of the NMeCH2OH group. Coupling of acetobromoglucose with HMPMM catalyzed by silver salts was not successful. Although Me and cyclohexyl derivs. of HMPMM may be produced in high yields by reaction of HMPMM with Me and cyclohexyl alcs. under acidic catalysis, prodn. of glycosides in this way gave poor yields. MNDO calcns. on reactions of HMPMM helped us devise improved reaction conditions for the condensation of 2,3,4,6-tetra-O-acetyl glucose with HMPMM and its derivs. The best procedure to generate one of the target glycosides is to react 2,3,4,6-tetra-O-acetyl glucose and formaldehyde with 2-methylamino-4,6-bis(dimethylamino)-1,3,5-triazine. The b-glycoside product was de-acetylated using potassium carbonate in dry methanol. . 3947-62-4 which is the cas registry number of one of substances is just one of reagents here..

Letter: Synthesis of glycosides in which the aglycon is an N-(hydroxymethyl)amino-1,3,5-triazine derivative

Letter: Synthesis of glycosides in which the aglycon is an N-(hydroxymethyl)amino-1,3,5-triazine derivative. Bagga, Kishore; Dua, Geeta; Williams, Gerallt; Simmonds, Richard J. ( Institute of Biological Sciences, University of Wales, Aberystwyth SY23 3DD, UK). Glycoconjugate Journal, 14(4), 519-521 (English) 1997 Chapman & Hall. CODEN: GLJOEW.Several substances like 3947-62-4 may be metioned in this study. ISSN: 0282-0080. DOCUMENT TYPE: Journal CA Section: 33 (Carbohydrates) The synthesis of analogs of the anti-tumor drug 2-[N-(hydroxymethyl)methylamino]-4,6-bis(dimethylamino)-1,3,5-triazine (HMPMM) in which the OH or a dimethylamino group is replaced by a carbohydrate has been explored. Triazinyl b-glycosides were readily prepd. by reaction of sugars with trimethyl-triazinylammonium salts. These were made with one or two methylamino groups on the triazine for reaction with formaldehyde to give the cytotoxic NMeCH2OH group. However, reaction of the triazinyl glycosides with formaldehyde gave complex intractable mixts. When the carbohydrate portion was changed to the fully protected 2,3,4,6-tetra-O-acetyl glucose a good yield of the 2-[N-(hydroxymethyl)methylamino]-4-(dimethylamino)-1,3,5-triazin-2-yl tetra-O-acetyl b-glucoside was obtained. However, de-acetylation using sodium methoxide also removed the N-CH2OH group. We are investigating protection of the base-sensitive N-CH2OH group as trialkylsilyl and benzyl ethers and are looking at de-acetylation methods that are more selective. We have prepd. glycosides in which the sugar is joined through the oxygen of the NMeCH2OH group. Coupling of acetobromoglucose with HMPMM catalyzed by silver salts was not successful. Although Me and cyclohexyl derivs. of HMPMM may be produced in high yields by reaction of HMPMM with Me and cyclohexyl alcs. under acidic catalysis, prodn. of glycosides in this way gave poor yields. MNDO calcns. on reactions of HMPMM helped us devise improved reaction conditions for the condensation of 2,3,4,6-tetra-O-acetyl glucose with HMPMM and its derivs. The best procedure to generate one of the target glycosides is to react 2,3,4,6-tetra-O-acetyl glucose and formaldehyde with 2-methylamino-4,6-bis(dimethylamino)-1,3,5-triazine. The b-glycoside product was de-acetylated using potassium carbonate in dry methanol. . 3947-62-4 which is the cas registry number of one of substances is just one of reagents here..