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- W2051648133 abstract "The synthesis of 3-O-carbamoyl-noviose, the carbohydrate of the antibiotic novobiocin, is described. Starting with D-glucose the synthesis comprises a number of steps (1–5) up to the important intermediate 3,5,6-tri-O-benzyl-2-O-methyl-D-galactono-γ-lactone (5), which was obtained by an intramolecular WALDEN inversion of 3,5,6-tri-O-benzyl-4-O-mesyl-2-O-methyl-D-glucono-N-methylamide (4). Compound 5 shows the correct steric arrangement of the asymmetric centres with respect to noviose. Successive transformations (6–10) led to the synthesis of noviose and finally (9–14) to methyl 3-O-carbamoyl-α-novioside, which was identical with the substance obtained by acid catalysed methanolysis of the antibiotic novobiocin." @default.
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- W2051648133 date "1964-01-01" @default.
- W2051648133 modified "2023-09-26" @default.
- W2051648133 title "Novobiocin II. Die Synthese der 3-O-Carbamoyl-noviose" @default.
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- W2051648133 doi "https://doi.org/10.1002/hlca.19640470207" @default.
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