Preparation of 5'-triphosphoryladnylyl-(2'-5')-adenylyl-(2'-5')-adenosine

Abstract

Abstract PURPOSE: To prepare the titled compound having protein-synthesis inhibiting activity and useful as a carcinostatic agent, etc., by the total synthesis which comprises the conversion of the (2'-5')oligomer of adenosine-5'-monophosphate having a 3'-OH group protected with a specific group to 5'-triphosphate, and the elimination of the protecting group from the product. CONSTITUTION: The objective compound of formula III (A is adenylyl) is prepared by (1) converting the (2'-5')oligomer of the adenosine-5'-mono-phosphate of formula II (NB is o-nitrobenzyl; n is 0, 1 or 2) to the 5'-triphosphate, and (2) eliminating the protecting group of the 3'-OH group. The oligomer of formula II can be prepared by converting the 3'-OH group of a compound of formula I (X is acyl or substituted or unsubstituted trityl) to o-nitro-4- and/or 5-substituted or unsubstituted benzyl group. The conversion to 5'-triphosphate is preferably carried out by reacting the oligomer with 1,1'-carbonylimidazole, and treating the reaction product with pyrophosphoric acid salt. The elimination of the protecting group is carried out preferably by the irradiation with ultraviolet rays having wavelength of ≥ 280nm. COPYRIGHT: (C)1981,JPO&Japio

Inventors

• 👤 Morio Ikehara

Bibliographic Details