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- W2016031087 abstract "After Hakomori methylation of 2-acetamido-2-deoxy-d-glucitol, the expected 2-deoxy-1,3,4,5,6-penta-O-methyl-2-(N-methylacetamido)-d-glucitol (3) was identified by g.l.c.-m.s. as the major product, and two minor products, 2-acetamido-2-deoxy-1,3,4,5,6-penta-O-methyl-d-glucitol (2) 2-deoxy-1,3,4,5,6-penta-O-methyl-2-(N-methylpropionamido)-d-glucitol (4), were present. The proportions and yields of these products were dependent on the reagent (sodium or potassium hydride) used for the preparation of the methylsulfinylmethanide. On Hakomori methylation of 2 and 3, the N-methylpropionamido (4)-methylisobutyramido, and traces of the N-methylpivalamido derivatives of 2-deoxy-1,3,4,5,6-penta-O-methyl-d-glucitol were formed. Using trideuteriomethyl iodide for methylation (e.g., of 3), it was found by g.l.c.-m.s. that the newly introduced methyl group(s) were located at the β-carbon of the N-methylacetamido group. Analogous results were obtained with 2-deoxy-4-O-[2[deoxy[3,4,6-tri-O-methyl-2-(N-methylacet-amido)-β-d-glucopyranosyl]-1,3,5,6,-tetra-O-methyl- 2-(N-methylacetamido)-d-glucitol." @default.
- W2016031087 created "2016-06-24" @default.
- W2016031087 creator A5090284235 @default.
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- W2016031087 date "1986-09-01" @default.
- W2016031087 modified "2023-10-17" @default.
- W2016031087 title "2-deoxy-1,3,4,5,6-penta-O-methyl-2-(N-methylacetamido)-d-glucitol and derivatives undergo C-emthylation at the N-methylacetamido group on repeated hakomori methylation" @default.
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- W2016031087 doi "https://doi.org/10.1016/s0008-6215(00)90289-1" @default.
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