1-Naphthol → HCID 91206009, compound

HRID 1889604Notes

Reaction equation

HRID 1889604 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[O:12][C@@H:11]([N:23]2[C:41]3[N:40]=[CH:39][N:38]=[C:27]([O:28][C:29]4[CH:34]=[CH:33][C:32]([N+]([O-])=O)=[CH:31][CH:30]=4)[C:26]=3[N:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1(OC2C3N=CN(C=3N=CN=2)[C@@H]2O[C@H](CO[Si](C(C)(C)C)(C)C)[C@@H](O[Si](C(C)(C)C)(C)C)C2)[C:46]2[CH:47]=CC=[CH:50][C:45]=2N=N1.C([O-])([O-])=O.[Cs+].[Cs+].C1(O)C2C(=CC=CC=2)C=CC=1>COCCOC>[Si:16]([O:15][C@@H:14]1[C@@H:13]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3])[O:12][C@@H:11]([N:23]2[C:41]3[N:40]=[CH:39][N:38]=[C:27]([O:28][C:29]4[C:34]5[C:33](=[CH:50][CH:45]=[CH:46][CH:47]=5)[CH:32]=[CH:31][CH:30]=4)[C:26]=3[N:25]=[CH:24]2)[CH2:10]1)([C:19]([CH3:21])([CH3:22])[CH3:20])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 70051-NaphtholHCID 10796Cesium carbonateHCID 24805984HCID 24805984, compoundHCID 91289782HCID 91289782, compound

Product 1

HCID 91206009HCID 91206009, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

As described for the synthesis of 3′,5′-bis-O-(tert-butyldimethylsilyl)-O6-(4-nitrophenyl)-2′-deoxyinosine, this naphthyl derivative was prepared by a reaction between O6-(benzotriazol-1-yl)-3′,5′-bis-O-(tert-butyldimethylsilyl)-2′-deoxyinosine (26) (59.8 mg, 0.100 mmol), Cs2CO3 (65.2 mg, 0.200 mmol) and 1-naphthol (15.9 mg, 0.110 mmol) in dry DME (1.0 mL) at 85° C. for 2 h. Chromatographic purification (SiO2, elution with 20% EtOAc in hexanes) afforded 49.2 mg (81% yield) of the title compound as a yellowish-white foam. Rf (20% EtOAc in hexanes)=0.37. 1H NMR (500 MHz, CDCl3): δ 8.44 (s, 1H, Ar—H), 8.41 (s, 1H, Ar—H), 7.93 (d, 1H, Ar—H, J=8.8), 7.91 (d, 1H, Ar—H, J=8.3), 7.81 (d, 1H, Ar—H, J=8.3), 7.54 (t, 1H, Ar—H, J=7.8), 7.50 (t, 1H, Ar—H, J=7.6), 7.42 (t, 1H, Ar—H, J=7.6), 7.39 (d, 1H, Ar—H, J=7.3), 6.56 (t, 1H, H-1′, J=6.4), 4.67 (m, 1H, H-3′), 4.06 (q, 1H, H-4′, J=3.4), 3.92 (dd, 1H, H-5′, J=11.2, 4.4), 3.82 (dd, 1H, H-5′, J=11.2, 2.9), 2.71 (quint, 1H, H-2′, J=6.3), 2.50 (ddd, 1H, H-2′, J=12.9, 5.9, 4.1), 0.94, 0.93 (2 s, 18H, tert-Bu), 0.12 (s, 12H, SiCH3). 13C NMR (126 MHz, CDCl3): δ 160.7, 152.7, 152.1, 148.6, 141.7, 134.9, 127.9, 127.3, 126.4, 126.2, 125.9, 125.5, 122.0, 121.9, 118.1, 88.1, 84.7, 71.9, 62.8, 41.4, 25.9, 25.7, 18.4, 18.0, −4.7, −4.8, −5.4, −5.5. FAB HRMS calcd for C32H47N4O4Si2 (M++H) 607.3136. found 607.3120.

Workup

  1. customChromatographic purification (SiO2, elution with 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5ab6bc23667a4faa9eb7c18106258496
Source dataset
uspto-grants-2013_08
Patent number
US08501931B2

Reaction notes

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