Thymidine → 2,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-

HRID 1372798

Reaktionsgleichung

Reaktionsgleichung von HRID 1372798
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3](O)[CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH3:16][C:15]1[C:13](=[O:14])[N:12]=[C:10]2[N:9]([C@@H:1]3[O:8][C@H:5]([CH2:6][OH:7])[C@H:3]([O:11]2)[CH2:2]3)[CH:17]=1

Komponenten

3

Edukt 2

HCID 5789ThymidineHCID 11776Triphenylphosphine

Produkt 1

HCID 4579822,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-

Versuchsvorschrift

There are a variety of known techniques for converting a nucleoside into an anhydronucleoside. For example, the anhydronucleoside can be prepared by mixing thymidine with triphenylphosphine and azeotropically drying with portions of acetonitrile (MeCN). The resulting mass is suspended in MeCN and then cooled. The mixture is rapidly stirred and diisopropylazodicarcobxylate in MeCN is added dropwise to the mixture. The resulting mixture is treated with water to form a suspension that is filtered to afford anhydrothymidine. (Grierson, J. R., Shields, A. F., Nuclear Medicine and Biology, 2000, 27 143–156; Balagopala, M. I., Ollapally, A. P., and Lee, H. J., Nucleosides-Nucleotides, 1996, 15(4) 899–906).

Aufarbeitung

  1. dry with materialazeotropically drying with portions of acetonitrile (MeCN)
  2. temperaturecooled
  3. additionis added dropwise to the mixture
  4. additionThe resulting mixture is treated with water
  5. customto form a suspension that
  6. filtrationis filtered

Quellen und Nachweise

ORD-Eintrag
ord-6b9d02c5ab4d497aba217ade05e51908
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160537B2

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