A novel synthesis of sulfamoyl nucleosides

The Biotin Repressor: Modulation of Allostery by Corepressor Analogs

“…The synthesis of 2 0 ,3 0 -O-isopropylidene-5 0 -Osulfamoyladenosine was as described by Kristinson, 36 with slight modifications, from the commercially available 2 0 ,3 0 -O-isopropylideneadenosine. The product was purified by silica gel chromatography with an elution gradient of methanol in ethyl acetate (0% -5%, v/v).…”

Herbicidally Active Sulfamoyl Nucleosides

“…36 Using the usual Vorbruggen conditions in conjunction with purine bases only the cyclised product 48 was obtained. 36 The crucial modification in reaction conditions, leading to the desired compounds in high yields, was the presence of a tertiary base in the reaction mixture.…”

“…36 Using the usual Vorbruggen conditions in conjunction with purine bases only the cyclised product 48 was obtained. 36 The crucial modification in reaction conditions, leading to the desired compounds in high yields, was the presence of a tertiary base in the reaction mixture. Drying the solvent became unneccessary, and prior silylation of the purine base could be dispensed with 36 For low melting (<120 °C) purine bases simply melting the base together with 47 led to good yields of the product.…”

“…36 The crucial modification in reaction conditions, leading to the desired compounds in high yields, was the presence of a tertiary base in the reaction mixture. Drying the solvent became unneccessary, and prior silylation of the purine base could be dispensed with 36 For low melting (<120 °C) purine bases simply melting the base together with 47 led to good yields of the product. The 2,6-diamino derivative 26 (Table Hie) The coupled products 50, 20, 51, and 13 could be further derivatised at C6, allowing a considerable diversification from a late intermediate (Table II) Displacement of the 6-chloro group from 53 37 (Fig.…”

“…The cytosine and uridine derivatives 40 and 41 (Table I) were inactive. Similarly, a number of benztriazole, benzimidazole, and triazole derivatives, 36 which were prepared according to fig. 3, were inactive.…”