Reaktion #82912

ord-b5ecf019055e48148398fb13f28e11ff

Reaktionsgleichung

Cc1cn([C@@]2([Si](C)(C)C(C)(C)C)C[C@H](ON)[C@@H](CO)O2)c(=O)[nH]c1=O
3'-O-Amino-(t-butyldimethylsilyl)thymidine
C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]
(Bu)4NF THF
→
Cc1cn([C@H]2C[C@H](ON)[C@@H](CO)O2)c(=O)[nH]c1=O
compound 4
Ausbeute 72.0%
Cc1cn([C@H]2C[C@H](ON)[C@@H](CO)O2)c(=O)[nH]c1=O
3'-O-Aminothymidine
Ausbeute 72.0%

Edukte

Cc1cn([C@@]2([Si](C)(C)C(C)(C)C)C[C@H](ON)[C@@H](CO)O2)c(=O)[nH]c1=O
3'-O-Amino-(t-butyldimethylsilyl)thymidine
C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]
(Bu)4NF THF

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

3'-O-Amino-(t-butyldimethylsilyl)thymidine was deblocked with (Bu)4NF/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 (2m, 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'HM), 6.2 (br s, 2 NH2), 7.48 (s, 1, C6H), and 11.24 (br s, 1, NH).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05623070uspto-grants-1997_04