| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345606 | Tetrahedron: Asymmetry | 2016 | 10 Pages |
Stable amides and oligopeptides derived from methyl trans,trans-3-azido-4-hydroxymethyl-l-azetidine carboxylate, prepared in 19% yield from diacetone allose, is the first example of a β-amino-azetidine carboxylic acid incorporated into peptidomimetics and provides a scaffold for investigating secondary structure induced by a novel β-amino acid. A number of azetidine iminosugars containing a NHAc substituent were prepared but none of them were β-N-acetylhexosaminidase inhibitors.
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3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-d-glucofuranoseC12H19N3O5[α]D20 = −47.5 (c 1.2, CHCl3)Source of chirality: d-glucose
3-Azido-3-deoxy-1,2-O-isopropylidene-α-d-glucofuranoseC9H15N3O5mp: 80–82 °C[α]D20 = −32.7 (c 0.47 in CHCl3)Source of chirality: d-glucose
3-Azido-3-deoxy-1,2-O-isopropylidene-α-d-xylofuranoseC8H13N3O4mp 68–70 °C[α]D20 = −57.8 (c 0.38 in CHCl3)Source of chirality: d-glucose
3-Azido-3-deoxy-d-xylopyranoseC5H9N3O4mp 72–74 °CSource of chirality: d-glucose
3-Azido-3-deoxy-1,2,4-tri-O-acetyl-d-xylopyranoseC11H15N3O7mp 46–48 °CSource of chirality: d-glucose
Methyl 3-azido-3-deoxy-2,4-di-O-acetyl-β-d-xylopyranosideC10H15N3O6[α]D20 = −65.0 (c, 0.72 in CHCl3)Source of chirality: d-glucose
Methyl 3-azido-3-deoxy-β-d-xylopyranosideC6H11N3O4mp 48–50 °C[α]D20 = −31.1 (c, 0.55 in CHCl3)Source of chirality: d-glucose
Methyl 3-azido-N-benzyl-2,3,4-trideoxy-2,4-imino-β-l-ribosideC13H16N4O2[α]D20 = −47.4 (c 0.72 in CHCl3)Source of chirality: d-glucose
Methyl 3-azido-N-benzyl-2,4-imino-2,3,4-trideoxy-l-ribonateC13H16N4O3[α]D20 = −39.6 (c, 0.50 in CHCl3)Source of chirality: d-glucose
Methyl 3-azido-N-benzyl-2,4-imino-2,3,4-trideoxy-l-ribonamideC13H17N5O2[α]D20 = −10.5 (c, 0.50 in CHCl3)Source of chirality: d-glucose
Methyl 3-acetamido-N-benzyl-2,4-imino-2,3,4-trideoxy-l-ribonamideC15H21N3O3[α]D20 = +56.4 (c, 0.90 in CHCl3)Source of chirality: d-glucose
Methyl 3-acetamido-2,4-imino-2,3,4-trideoxy-l-ribonamideC8H15N3O3[α]D20 = +112.5 (c 0.30 in CHCl3)Source of chirality: d-glucose
3-Azido-N-benzyl-1,5-di-O-acetyl-2,4-imino-2,3,4-trideoxy-meso-ribitolC16H20N4O4[α]D20 = 0 (c 0.81 in CHCl3)Source of chirality: d-glucose
3-Acetamido-N-benzyl-1,5-di-O-acetyl-2,4-imino-2,3,4-trideoxy-meso-ribitolC18H24N2O5[α]D20 = 0 (c 1.0 in CHCl3)Source of chirality: d-glucose
3-Acetamido-N-benzyl-2,4-imino-2,3,4-trideoxy-meso-ribitolC14H20N2O3[α]D20 = 0 (c 1.2 in MeOH)Source of chirality: d-glucose
3-Acetamido-2,4-imino-2,3,4-trideoxy-meso-ribitolC7H14N2O3[α]D20 = 0 (c 1.0 in H2O)Source of chirality: d-glucose
Methyl 3-azido-N-benzyl-5-O-(tert-butyldimethylsilyl)-2,4-imino-2,3,4-trideoxy-l-ribonateC19H30N4O3Si[α]D20 = +55 (c 0.36 in CHCl3)Source of chirality: d-glucose
