Structure of the product from a novel cyclization reaction involving a C(6)-substituted uridine analog.
5,6,7,7a,9,10,14b,14c-Octahydro-4-[2,3-O-(1-methylethylidene )-beta-D- ribofuranosyl]cyclopenta-[4,5]pyrimido[5',4':3,4]pyrrolo[2,1- a]isoquinoline-1,3(2H,4H)-dione, C25H31N3O6, M(r) = 469.54, tetragonal, P4(3)2(1)2, a = 12.577 (2), b = 12.577 (2), c = 29.893 (4) A, V = 4729 (1) A3, Z = 8, Dx = 1.319 g cm-3, lambda (Cu K alpha) = 1.5418 A, mu = 7.9 cm-1, F(000) = 2000, T = 298 K, final R = 0.038, wR = 0.064 for all 1884 independent reflections and 432 variables. The crystal structure shows a syn conformation around the N(1)--C(1') single bond, consistent with other C(6)-substituted uridine analogs, and an unusual O(1') endo conformation of the ribose ring. The stereochemistries of the three newly created chiral centers are 14cR, 4aR, 7aS.
Wang
B
B
Department of Chemistry, University of Kansas, Lawrence 66045.
Takusagawa
F
F
Mertes
M P
MP
Bowman-James
K
K
D018360:Crystallography, X-Ray; D003500:Cyclization; D007546:Isoquinolines / Q000737:chemistry*; D008968:Molecular Conformation; D014529:Uridine / Q000031:analogs & derivatives* / Q000737:chemistry
D007546:Isoquinolines; C084279:5,6,7,7a,9,10,14b,14c-octahydro-4-(2,3-O-(1-methylethylidene)-ribofuranosyl)cyclopenta(4,5)pyrimido(5',4':3,4)pyrrolo(2,1-a)isoquinoline-1,3(2H,4H)-dione; D014529:Uridine