HCID 15546043, compound → HCID 57227701, compound

HRID 1067894Notes

Reaction equation

HRID 1067894 reaction equation
C([O:9][C@@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@H:11]1[N:34]1[CH:39]=[CH:38][C:37](=[O:40])[N:36]=[CH:35]1)(=O)C1C=CC=CC=1.C[O-].[Na+].CO>N1C=CC=CC=1>[C@@H:11]1([N:34]2[CH:39]=[CH:38][C:37](=[O:40])[N:36]=[CH:35]2)[O:12][C@H:13]([CH2:24][OH:25])[C@@H:14]([OH:15])[C@H:10]1[OH:9]

Participants

4

Reactant 2

HCID 15546043HCID 15546043, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 57227701HCID 57227701, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Referring to FIG. 9, 1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-1,4-dihydropyrimidine-4-one (3) was synthesized in accordance with Niedballa et al., J. Org. Chem 1974, 39, 3668-3671. 1-(β-D-Ribofuranosyl)-1,4-dihydropyrimidine-4-one (5) was prepared by standard NaOMe/MeOH deprotection of derivative 3 with nearly quantitative yield. 1-(5-O-Dimethoxytrityl-β-D-Ribofuranosyl)-1,4-dihydropyrimidine-4-one (6) was prepared by standard dimethoxytritylation of 5 in pyridine (rt., overnight) resulting in a yield of 83%. 1-(5-O-Dimethoxytrityl-2-O-tert-butyldimethylsilyl-β-D-Ribofuranosyl)-1,4-dihydropyrimidine-4-one was prepared using standard silylation procedure (Hakimelahi et al., Can. J. Chem. 1982, 60, 1106-1113). 1-[5-O-Dimethoxytrityl-2-O-tert-butyidimethylsilyl-3-O-2cyanoethyl-N,N-diisopropylaminophosphoramidite-β-D-Ribofuranosyl]-1,4-dihydro-pyrimidine-4-one (7) was prepared by phosphitylation using standard phosphitylation procedure (Tuschl et al., Biochemistry 1993, 32, 11658-11668).

Workup

  1. customwas synthesized in accordance with Niedballa et al., J
  2. customresulting in a yield of 83%
  3. custom1-(5-O-Dimethoxytrityl-2-O-tert-butyldimethylsilyl-β-D-Ribofuranosyl)-1,4-dihydropyrimidine-4-one was prepared

Sources & evidence

ORD record
ord-8f441c9a17fa4a44aab388f090d2311e
Source dataset
uspto-grants-2001_06
Patent number
US06248878B1

Reaction notes

Loading…