
Collection of Czechoslovak Chemical Communications p. 395 - 406 (2000)
Update date:2022-08-05
Topics:
Hrebabecky, Hubert
Holy, Antonin
Tosylation of (±)-1-[trans-4-hydroxy-3,3-bis(hydroxymethyl)cyclopentyl]-5- methylpyrimidine-2(1H),4(3H)-dione (1) and (±)-1-[cis-4-hydroxy-3,3-bis(hydroxymethyl)cyclopentyl]-5- methylpyrimidine-2(1H),4(3H)-dione (2) and treatment of the obtained 1-[(1R(black star),3R(black star),4S(black star))-4-hydroxy-3-(hydroxymethyl)-3-[(tosyloxy) methyl]cyclopentyl]-5-met hylpyrimidine2(1H),4(3H)-dione (6) and 2-[(1R(black star),3S(black star),4R(black star))-4-hydroxy-3-(hydroxymethyl)-3-](tosyloxy)- methyl[cyclopentyl]-5-methylpyrimidine-2(1H),4(3H)-dione (9) with methanolic sodium methoxide gave 1-[(1R(black star),4S(black star),6S(black star))-4-hydroxymethyl-2-oxabicyclo[3.2.0]hept-6-yl] -5-methylpyrimidinf-2(1H),4(3H)-dione (7) and 1-[(1R(black star),4S(black star),6R(black star))-4-hydroxymethyl-2-oxabicyclo-[3.2.0]hept-6- yl]-5-methylpyrimidine-2(1H),4(3H)-dione (10), respectively. Treatment of (±)-1-[cis.v-4-mesyloxy-3,3-bis[(trityloxy)methyl]cyclopentyl]-5- methylpyrimidine-2(1H), 4(3H)-dione (11), which was prepared from 2 by tritylation and mesylation, with 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethylformamide afforded after deprotection (±)-1-[4,4-bis-(hydroxymethyl)cyclopent-2-en-1-yl]-5-methylpyrimidine- 2(1H),4(3H)-dione (14). Hydrogenation of 14 led to (±)-1-[3,3-bis(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2(1H),4(3H)- dione (15). (±)-1-[trans-4-Mesyloxy-3,3-bis[(trityloxy)methyl]cyclopentyl]-5- methylpyrimidine-2(1H),4(3H)-dione (17), which was prepared from 1, was converted to (1R(black star),9R(black star)(black star))-6-methyl-5-oxo-11,11-bis(trityloxymethyl)-2-oxa-4,8- diazatricyclo[7.2.1.03,8]dodec-3,6-diene (18). The compound 18 was deprotected and heated with lithium azide in dimethylformamide to give (±)-1-[trans-4-azido-3,3-bis(hydroxymethyl)cyclopentyl|-5- methylpyrimidine-2(1H),4(3H)-dione (21).
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(2000)