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- W2011154314 abstract "The rearrangement of methyl 3-azido-2-S-benzyl-3-deoxy-2-thio-α-D-altropyranoside (3) in methanol to give methyl 3-azido-2-S-benzyl-3-deoxy-2-thio-αβ-D-altrofuranoside (4a) was catalysed by Amberlite CG-120(H+) resin. Partial benzoylation of 4a gave the 6-O-benzoyl derivative (4b), the 5-O-toluene-p-sulphonyl derivative (4c) of which was converted into methyl 5,6-anhydro-3-azido-2-S-benzyl-3-deoxy-2-thio-αβ-L-galactofuranoside (7) with methanolic sodium methoxide. Reduction of 7 with lithium aluminium hydride gave the 3,6-dideoxy sugar (8a) which, with Raney nickel, gave methyl 3-amino-2,3,6-trideoxy-αβ-L-lyxo-hexofuranoside (9). Acid hydrolysis of 9 gave 3-amino-2,3,6-trideoxy-L-lyxo-hexose (daunosamine) which is a component of the antibiotic daunomycin." @default.
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- W2011154314 date "1977-12-01" @default.
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- W2011154314 title "Synthesis of daunosamine" @default.
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- W2011154314 doi "https://doi.org/10.1016/s0008-6215(00)83176-6" @default.
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