Methanol → 2-Deoxyribose, D-

For example, according to Examples of WO 2009/066447, the 3-cyanovinylcarbazole group in Formula (V) is produced by heating 3-iodocarbazole (3.52 mmol) and acrylonitrile (7.04 mmol) in dioxane to reflux in the presence of triphenylphosphine (0.53 μmol), palladium acetate (0.18 μmol), and triethylamine (4.23 mmol) at 75° C. for 11.5 hours. In those Examples, the binding between 3-cyanovinylcarbazole and deoxyribose is achieved by stirring 3-cyanovinylcarbazole (1.20 mmol) and Hoffer's chlorosugar (prepared by replacing the hydroxyl group at 1-position of deoxyribose with chlorine, and the hydroxyl groups at 3-position and 6-position of the deoxyribose with a p-toluoyloxy group) (1.24 mmol) in acetonitrile in the presence of KOH (3.87 mmol) and TDA-1 (34 μmol) at room temperature for 20 minutes, and then adding NaOMe (1.2 mmol) in methanol to the resulting mixture, followed by stirring the resulting mixture at room temperature for 3.5 hours to deprotect the hydroxyl groups at 3-position and 6-position of the deoxyribose. According to the method described in Takehiro Ami et al., Organic & Biomolecular Chemistry 5: 2583-2586 (2007), the binding product between p-carbamoylvinylphenol and deoxyribose is similarly produced by reacting p-iodophenol with Hoffer's chlorosugar to bind them together and then reacting the resulting product with methyl methacrylate. According to the method described in Akio Kobori et al., Chemistry Letters 38: 272-273 (2009), the binding product between 4,5′,8-trimethylpsoralen and deoxyribose is similarly produced by reacting 3-iodo-4,5′,8-trimethylpsoralen with Hoffer's chlorosugar. According to the method described in Kenzo Fujimoto et al., Chemical Communications: 3177-3179 (2005), the binding product between N3-methyl-5-cyanovinyluracil and deoxyribose is similarly produced by reacting 2-iodo-N3-methyluridine with acrylonitrile. Also, when a sugar other than deoxyribose (e.g., ribose) is used, a binding product between the photoreactive group and the sugar can be similarly obtained.

1. customprepared

ORD record

ord-92a3c8c9c6254e64b8b9fe3ee19b2f38

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09416403B2