3'-O-Amino-(t-butyldimethylsilyl)thymidine → 3'-o-Aminothymidine

HRID 1955832

Reaction equation

HRID 1955832 reaction equation
[NH2:1][O:2][C@@H:3]1[C@@H:7]([CH2:8][OH:9])[O:6][C@@:5]([Si](C(C)(C)C)(C)C)([N:10]2[CH:18]=[C:16]([CH3:17])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:4]1>C1COCC1>[NH2:1][O:2][C@@H:3]1[C@@H:7]([CH2:8][OH:9])[O:6][C@@H:5]([N:10]2[CH:18]=[C:16]([CH3:17])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:4]1

Participants

3

Reactant 1

HCID 691018933'-O-Amino-(t-butyldimethylsilyl)thymidine

Product 1

HCID 1904883'-o-AminothymidineYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3'-O-Amino-(t-butyldimethylsilyl)thymidine was deblocked with (Bu)4 NF/THF in standard way to furnish compound 4 (72%). Crystallized from ether/hexanes/ethanol as fine needles, mp 81° C. 1H NMR (Me2SO--d6) δ1.78 (s, 3, CH3), 2.17 and 2.45 (2 m, 2, 2'CH2), 3.70 (m, 2, 5'CH2), 3.88 (m, 1, 4'H), 4.16 (m, 1, 3'H), 4.8 (br s, 1, 5'OH), 6.05 (dd, 1, 1'H), 6.2 (br s, 2 NH2), 7.48 (s, 1, C6H), and 11.24 (br s, 1, NH). Anal. Calcd. for C10 H15N3O5 : C, 46.69; H, 5.87; N, 16.33; found: C, 46.55; H, 5.91; N, 16.21.

Sources & evidence

ORD record
ord-22d2ed9e65cf404e9201abc44b183f8b
Source dataset
uspto-grants-1998_07
Patent number
US05777092

Linked notes

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