Deoxyadenosine → (2s,3r,5s)-5-(6-Amino-9h-Purin-9-Yl)-Tetrahydro-2-(Hydroxymethyl)furan-3-Ol

HRID 928705

Reaction equation

HRID 928705 reaction equation
[CH2:1]1[C@H:5]([N:6]2[C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:15])[C:9]=3[N:8]=[CH:7]2)[O:4][C@H:3]([CH2:16][OH:17])[C@H:2]1[OH:18]>O>[CH2:1]1[C@@H:5]([N:6]2[C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:15])[C:9]=3[N:8]=[CH:7]2)[O:4][C@@H:3]([CH2:16][OH:17])[C@@H:2]1[OH:18]

Participants

3

Reactant 1

HCID 13730Deoxyadenosine2×

Product 1

HCID 489519(2s,3r,5s)-5-(6-Amino-9h-Purin-9-Yl)-Tetrahydro-2-(Hydroxymethyl)furan-3-Ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1H NMR (200 MHz, DMSO-D6): δ 8.35 and 8.14 (2s, 2H, H2 and H8), 7.34 (sl, 2H, NH2), 6.35 (dd, 1H, H1′, J 6.1 Hz, J 7.85 Hz), 5.33 (d, 1H, OH2′, J 4.0 Hz), 5.28 (dd, 1H, H3′, J 4.95 Hz; J 6.6 Hz), 4.42 (m, 1H, OH5′), 3.88 (m, 1H, H4′), 3.63-3.52 (m, 2H, H5′a and H5′b), 2.71 (m, 1H, H2′a), 2.28 (m, 1H, H2′b). (identical to commercial 2′-deoxy-D-adenosine) αD+26° (c 0.5 water) (commercial 2′-deoxy-D-adenosine-25° (c 0.5 water)).

Sources & evidence

ORD record
ord-721327ea68f54a499ec95122a82c4ce3
Source dataset
uspto-grants-2016_03
Patent number
US09290533B2

Linked notes

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