Chlorotrimethylsilane → HCID 136132501, compound

HRID 264719Notes

Reaction equation

HRID 264719 reaction equation
[CH2:1]([O:6][C@@H:7]1[C@H:11]([OH:12])[C@@H:10]([CH2:13][OH:14])[O:9][C@H:8]1[N:15]1[C:25]2[N:24]=[C:22]([NH2:23])[NH:21][C:19](=[O:20])[C:18]=2[N:17]=[CH:16]1)[CH2:2][CH2:3][CH2:4][CH3:5].C[Si](Cl)(C)C.[C:31](Cl)(=[O:35])[CH:32]([CH3:34])[CH3:33]>N1C=CC=CC=1>[C:31]([NH:23][C:22]1[NH:21][C:19](=[O:20])[C:18]2[N:17]=[CH:16][N:15]([C:25]=2[N:24]=1)[C@@H:8]1[O:9][C@H:10]([CH2:13][OH:14])[C@@H:11]([OH:12])[C@H:7]1[O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])(=[O:35])[CH:32]([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 62325Isobutyryl chlorideHCID 136205272HCID 136205272, compound

Product 1

HCID 136132501HCID 136132501, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2'-O-pentylguanosine (2.3 g) in pyridine (35 ml) was treated with trimethylsilyl chloride (4.15 ml, 5 eq) and isobutyryl chloride (3.4 ml, 5 eq) as per the procedure of Example 4 to yield the product as a foam (2.3 g). An analytical sample was crystallized from EtOAc/Hex. m.p. 178°-180° C. 1H NMR (DMSO-d6) δ 0.75 (t, 3, CH3), 1.1 [m, 10, 2×CH2, CH(CH3)2 ], 1.4 (m, 2, CH2), 2.74 [m, 1, CH(CH3)2 ], 3.56 (m, 4, OCH2, H-5'), 3.93 (m, 1, H-4'), 4.25 (m, 1), 4.34 (m, 1), 5.05 (t, 1, 5'-OH), 5.17 (d, 1, 3'-OH) 5.88 (d, 1, H-1'), 8.27 (s, 1, H-8), 11.65 (br s, 1, NH) and 12.05 (br s, 1, NH). Anal. Calcd. for C19H29N5O6 : C, 53.89; H, 6.90; N, 16.54. Found: 53.75; H, 6.92; N, 16.40

Sources & evidence

ORD record
ord-91a2115935aa4a62b457355f7c6a8b2d
Source dataset
uspto-grants-1997_07
Patent number
US05646265

Reaction notes

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