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• W2056477162 abstract "The reaction between methyl 2,3-anhydro-5-O-p-nitrobenzoyl--β-d-ribofuranoside (2) and ammonia gives mainly the d-xylo amine 3, as previously reported. Azide ion shows similar regioselectivity with methyl 2,3-anhydro--β-d-ribofuranoside (1). Ammonia reacts with methyl 2,3-anhydro-5-O-p-nitrobenzoyl-α-d-ribofuranoside (11) to give the d-arabino amine 12 and d-xylo amine 13 in the ratio 2:1. Both isomers were obtained crystalline after chromatography on Dowex 1 (HO− resin. With nitrous acid, 3, 13, and 12 each yield the parent epoxide, together with other products. In particular, 12 gives 2-O-methyl-d-ribose 14 as the major product; the structure of 14 was proved by synthesis of the enantiomer 21. Conformational aspects of the deaminations are discussed." @default.
• W2056477162 created "2016-06-24" @default.
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• W2056477162 date "1977-08-01" @default.
• W2056477162 modified "2023-10-09" @default.
• W2056477162 title "Action of ammonia on the methyl 2,3-anhydro-d-ribofuranosides, and treatment of the products with nitrous acid" @default.
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• W2056477162 doi "https://doi.org/10.1016/s0008-6215(00)81922-9" @default.
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