ChemicalBook CAS DataBase List 2'-Deoxy-2'-fluoroguanosine

2'-Deoxy-2'-fluoroguanosine synthesis

12synthesis methods

Product Name:2'-Deoxy-2'-fluoroguanosine
CAS Number:78842-13-4
Molecular formula:C10H12FN5O4
Molecular Weight:285.23

The synthesis of 2'-deoxy-2'-fluoroguanosine was accomplished using tetraisopropyldisiloxanyl (TPDS) protected 9-beta-D-arabinofuranosylguanine as starting material, and conversion to the intermediate diisobutyryl-arabinofuranosylguanosine. Deprotection of the TPDS group, was followed by protection of the hydroxyl group with THP to give diisobutyryl di-THP protected arabinofuranosylguanine. Selective O-deacylation and triflation was followed by treatment of the crude product with fluoride, then deprotection of the THP groups.

Guanosine, 2',3'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]- (9CI)

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Yield:-

Steps:

2'-Fluorodeoxyguanosine

[0155] The synthesis of 2?-deoxy-2?-fluoroguanosine was accomplished using tetraisopropyldisiloxanyl (TPDS) protected 9-beta-D-arabinofuranosylguanine as starting material, and conversion to the intermediate isobutyryl-arabinofuranosylguanosine. Alternatively, isobutyryl-arabinofuranosylguanosine was prepared as described by Ross et al., (Nucleosides & Nucleosides, 16, 1645, 1997). Deprotection of the TPDS group was followed by protection of the hydroxyl group with THP to give isobutyryl di-THP protected arabinofuranosylguanine. Selective O-deacylation and triflation was followed by treatment of the crude product with fluoride, then deprotection of the THP groups. Standard methodologies were used to obtain the 5?-DMT- and 5?-DMT-3?-phosphoramidites.

References:

US2003/225013,2003,A1 Location in patent:Page 18

80681-25-0 Synthesis