HCID 10984692, compound → 7-DEAZA-7-IODO-2'-DEOXYGUANOSINE

HRID 1611442Notes

Reaction equation

HRID 1611442 reaction equation
CC(C)C([O:5][C@@H:6]1[C@@H:10]([CH2:11][O:12]C(=O)C(C)C)[O:9][C@@H:8]([N:18]2[C:22]3[N:23]=[C:24]([NH:29]C=O)[N:25]=[C:26]([O:27]C)[C:21]=3[C:20]([I:32])=[CH:19]2)[CH2:7]1)=O>CC#N>[NH2:29][C:24]1[NH:25][C:26](=[O:27])[C:21]2[C:20]([I:32])=[CH:19][N:18]([C@@H:8]3[O:9][C@H:10]([CH2:11][OH:12])[C@@H:6]([OH:5])[CH2:7]3)[C:22]=2[N:23]=1

Participants

3

Reactant 1

HCID 10984692HCID 10984692, compound

Product 1

HCID 1354052527-DEAZA-7-IODO-2'-DEOXYGUANOSINE

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (58) is prepared in analogy with Example 51 by proceeding from compound (46) (200 mg, 0.35 mmol). Colorless crystals (126 mg, 92%) are obtained from MeCN. Melting point: 218-220° C. UV (MeOH): λmax 266 (12,000), 285 (sh, 8400). 1H-NMR ([D6] DMSO): δ=2.08 (m, Hα—C(2′)), 2.30 (m, Hβ—C(2′)), 3.48 (m, H—C(5′)), 3.74 (m, H—C(4′)), 4.26 (m, H—C(3′)), 4.89 (t, 5′-OH), 5.18 (d, 3′-OH), 6.25 (dd, H—C(1′)), 6.34 (br., NH2), 7.09 (s, H—C(6)), 10.51 (br., NH). Anal. calculated for C11H13IN4O4 (392.2): C 33.69, H 3.34, N 14.29; found: C 33.78, H 3.42, N 14.29.

Sources & evidence

ORD record
ord-8df3959407c941e0b665055072f32b01
Source dataset
uspto-grants-2006_01
Patent number
US06987177B2

Reaction notes

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