Table 2.
Summary table of neoglycosides synthesized and tested.
| Neoglycoside (see Figure 1) | Sugars utilized | Yield | α/β ratio |
|---|---|---|---|
| Dx01 | D-glucose (5)b | 46% | β only |
| Dx02 | D-xylose (6)b | 69% | β only |
| Dx03 | L-rhamnose (7)b | 66% | β only |
| Dx04 | D-galactose (8)b | 38% | β only |
| Dx05 | N-acetyl-D-glucosamine (9)b | 30% | β only |
| Dx06 | D-fucose (10)b | 25% | β only |
| Dx07 | D-ribose (11)b | 14% | α/β=1/4 |
| Dx08 | D-glucosamine hydrochloride (12)b | -a | -a |
| Dx09 | D-glucuronic acid (13)b | 45% | β only |
| Dx10 | 3-O-methyl-D-glucose (14)b | 51% | β only |
| Dx11 | L-glucose (15)b | 34% | β only |
| Dx12 | D-arabinose (16)b | 32% | α/β=1/5 |
| Dx13 | D-erythrose (17)b | 44% | α/β=3/1 |
| Dx14 | forosamine (18)c | 41% | β only |
| Dx15 | 2-deoxy-2-N-alloc-D-glucosamine (19)28 | 47% | α/β=1/1 |
| Dx16 | 6-deoxy-6-azido-D-glucose (20)b | 38% | β only |
| Dx17 | 2-deoxy-2-azido-D-glucose (21)b | 41% | α/β=1/1 |
| Dx18 | 3-deoxy-3-fluoro-D-glucose (22)b | 48% | β only |
| Dx19 | L-galactose (23)b | 48% | β only |
| Dx20 | D-cellobiose (24)b | 23% | β only |
| Dx21 | streptozocin (25)b | 11% | α/β=1/1 |
| Dx22 | digitoxose (26)b | 28% | β only |
| Dx23 | N-acetylmuramic acid (27)b | 32% | α/β=1/1 |
| Dx24 | 3-deoxy-3-N-decanoyl-D-glucosamine (28)20a | -a | -a |
| Dx25 | 6-deoxy-6-N-decanoyl-D-glucosamine (29)20a | 18% | β only |
| Dx26a | 2-deoxy-2-azido-D-glucose (21)b | 20% 2 steps | α only |
| Dx26b | 2-deoxy-2-azido-D-glucose (21)b | 22% 2 steps | β only |
| Dx27 | 6-deoxy-6-azido-D-glucose (20)b | 25% 2 steps | β only |
| Dx28 | 2,3,4,6-tetraacetyl-D-glucose (30)c | -a | -a |
| Dx29 | 2-deoxy-2-fluoro-D-glucose (31)b | 21% | β only |
| Dx30 | D-mannose (32)b | 27% | α/β=1/2 |
| Dx31 | 2-deoxy-2-azido-D-mannose (33) 29 | 32% | α/β=1/1 |
| Dx32 | 2-deoxy-2-azido-D-mannose (33) 29 | 35% 2 steps | α/β=1/1 |
| Dx33 | 2-deoxy-2-azido-D-galactose (34) 29 | 31% | β only |
| Dx34 | 2-deoxy-2-azido-D-galactose (34) 29 | 31% 2 steps | β only |
| Dx35 | 2-deoxy-2-N-methyl-D-glucosamine (35)30 | -a | -a |
| Dx36 | 2-deoxy-2-N-dimethyl-D-glucosamine (36)30 | -a | -a |
| Dx37 | 2-deoxy-2-N-trifluoroacetyl-D-glucosamine (37)30 | 22% | β only |
| Dx38 | 2-deoxy-D-glucose (38)b | 37% | α/β=1/1 |
| Dx39 | 2-deoxy-2-azido-D-xylose (39)c | 37% | β only |
| Dx40 | 2-deoxy-2-azido-D-xylose (39)c | 30% 2 steps | β only |
| Dx41 | 4-deoxy-4-azido-L-ribose (40)c | 33% | β only |
a
no reaction
b
commercially available
c
synthesized in this work