| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349855 | Tetrahedron: Asymmetry | 2009 | 4 Pages |
Cyclisation by double reductive amination of 2-acetamino-2-deoxy-d-xylo-hexos-5-ulose with N-2 protected l-lysine derivatives provided 2-acetamino-1,2-dideoxynojirimycin derivatives without any observable epimer formation at C-5. Modifications on the lysine moiety gave access to lipophilic derivatives that exhibited improved hexosaminidase inhibitory activities.
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Methyl (5S)-2-acetamino-5-C-benzyloxy-2-deoxy-β-d-xylo-hexopyranosideC16H23NO7Ee = 100%[α]D20=-19.8 (c 1.1, MeOH)Source of chirality: 2-acetamino-2-deoxy-d-glucose
Methyl-N6-(2-acetamino-1,2,5-trideoxy-d-glucitol-1,5-diyl)-N2-tert-butyloxycarbonyl-l-lysinateC20H37N3O8Ee = 100%[α]D20=+1.2 (c 1.1, MeOH)Source of chirality: 2-acetamino-2-deoxy-d-glucose
Methyl-N6-(2-acetamino-1,2,5-trideoxy-d-glucitol-1,5-diyl)-N2-dansyl-l-lysinateC27H40N4O8SEe = 100%[α]D20=+16.6 (c 1.3, MeOH)Source of chirality: 2-acetamino-2-deoxy-d-glucose
Methyl 6-[N6-(2-acetamino-1,2,5-trideoxy-d-glucitol-1,5-diyl)-N2-tert-butyloxycarbonyl-l-lysinyl]aminohexanoateC26H48N4O9Ee = 100%[α]D20=+3.0 (c 1.8, MeOH)Source of chirality: 2-acetamino-2-deoxy-d-glucose
Methyl 6-[N6-(2-acetamino-1,2,5-trideoxy-d-glucitol-1,5-diyl)-N2-dansyl-l-lysinyl]aminohexanoateC33H51N5O9SEe = 100%[α]D20=+1.9 (c 0.9, MeOH)Source of chirality: 2-acetamino-2-deoxy-d-glucose
