Deoxycytidine → 5'-O-(tert-Butyldimethylsilyl)-2'-deoxycytidine

HRID 1363688Notes

Reaction equation

HRID 1363688 reaction equation
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19]>N1C=CC=CC=1>[Si:21]([O:7][CH2:6][C@H:5]1[O:8][C@@H:1]([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[CH2:2][C@@H:3]1[OH:4])([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 13711DeoxycytidineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 99783055'-O-(tert-Butyldimethylsilyl)-2'-deoxycytidineYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 2′-deoxycytidine 47 (1.00 g; 4.40 mmol) in dry pyridine (37 mL), TBDMSCl (814 mg; 5.39 mmol) was added. The mixture was stirred at room temperature for 20 h. After evaporation, the residue was purified by flash column chromatography using CH3OH—CH2Cl2 (1:10) as the eluent to afford 48 as white solid (1.26 g; 84% yield): 1H NMR (400 MHz, CD3OD) δ 8.03 (d, J=7.5 Hz, 1H, 6-H), 6.23 (t, J=6.3 Hz, 1H, 1′-H), 5.86 (d, J=7.5 Hz, 1H, 5-H), 4.35 (m, 1H, 3′-H), 3.91-3.98 (m, 2H, 4′-H and one of 5′-H), 3.85 (dd, J=2.5, 11.3 Hz, 1H, one of 5′-H), 2.36-2.43 (ddd, J=4.1, 6.1, 13.5 Hz, 1H, one of 2′-H), 2.05-2.13 (m, 1H, one of 2′-H), 0.94 (s, 9H, C(CH3)3), 0.14 (s, 3H, one of SiCH3), 0.13 (s, 3H, one of SiCH3); 13C NMR (100 MHz, CD3OD) δ 167.1, 157.6, 142.1, 95.6, 88.7, 87.4, 71.7, 64.1, 42.7, 26.5, 19.3, −5.2, −5.3; HRMS (FAB+) calcd for C15H28O4N3Si (M+H+): 342.1849, found: 342.1844.

Workup

  1. customAfter evaporation
  2. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-865053d371734165bfe2cbb3cfa69206
Source dataset
uspto-grants-2011_02
Patent number
US07883869B2

Reaction notes

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