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- W1566804557 abstract "The displacement reactions of 2,3-di-O-benzoyl-4,6-di-O-mesyl-α-D-glucopyranosyl 2,3-di-O-mesyl-α-D-glucopyranoside (1) with azide anion have been studied. In hexamethylphosphoric triamide, all four sulphonate groups were replaced to give the tetra-azide 4 with inversion of configuration at the 4,4′ positions. When N,N-dimethylformamide was used as the solvent, selective substitution of only the primary sulphonate groups in 1 occurred. The tetraazide 4 was debenzoylated to give 4,6-diazido-4,6-dideoxy-α-D-galactopyranosyl 4,6-diazido-4,6-dideoxy-α-D-galactopyranoside (5), which was reduced to the corresponding tetra-amine 6, characterized as the tetra-N-acetyl derivative. Similarly, 2,3,6-tri-O-benzoyl-4-O-mesyl-α-D-glucopyranosyl 2,3,6-tri-O-benzoyl-4-O-mesyl-α-D-glucopyranoside (2) underwent replacement of both sulphonate groups by azide to give, after debenzoylation, 4-azido-4-deoxy-α-D-galactopyranosyl 4-azido-4-deoxy-α-D-galactopyranoside (8). The p.m.r. spectra of the tetra-azido derivatives 4 and 5 were interpretable by first-order analysis and clearly showed that both rings had the galacto configuration and that both adopted the C41 conformation." @default.
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- W1566804557 date "1970-08-01" @default.
- W1566804557 modified "2023-10-18" @default.
- W1566804557 title "Chemical modification of trehalose" @default.
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- W1566804557 doi "https://doi.org/10.1016/s0008-6215(00)80485-1" @default.
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