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Methanol → Triethylammonium 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methyluridine-3'-O-succinate

HRID 891222
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 891222
[CH3:1][O:2][CH2:3][CH2:4][O:5][C@@H:6]1[C@H:10]([OH:11])[C@@H:9]([CH2:12][OH:13])[O:8][C@H:7]1[N:14]1[CH:21]=[C:20]([CH3:22])[C:18](=[O:19])[NH:17][C:15]1=[O:16].[CH3:23][O:24][C:25]1[CH:46]=[CH:45][C:28]([C:29](Cl)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:27][CH:26]=1.C[OH:48].[C:49]1(=[O:55])[O:54][C:52](=[O:53])[CH2:51][CH2:50]1>N1C(C)=CC=CC=1C.C(#N)C.C(N(CC)CC)C>[CH3:23][O:24][C:25]1[CH:46]=[CH:45][C:28]([C:29]([O:13][CH2:12][C@H:9]2[O:8][C@@H:7]([N:14]3[CH:21]=[C:20]([CH3:22])[C:18](=[O:19])[NH:17][C:15]3=[O:16])[C@H:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[C@@H:10]2[O:11][CH:51]([C:52]([O-:48])=[O:53])[CH2:50][C:49]([O-:54])=[O:55])([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:27][CH:26]=1.[CH2:21]([NH+:14]([CH2:7][CH3:6])[CH2:15][CH3:23])[CH3:20].[CH2:21]([NH+:14]([CH2:7][CH3:6])[CH2:15][CH3:23])[CH3:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 887MethanolHCID 7922Succinic anhydrideHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 112439882'-O-(2-Methoxyethyl)-5-methyl-uridine

Produkt 1

HCID 86593945Triethylammonium 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methyluridine-3'-O-succinateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 79372,6-LutidineLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

2′-O-(2-methoxyethyl)-5-methyluridine (MOE T, 15.8 g, 50 mmol) was dissolved in 2,6-lutidine (23.3 ml) and acetonitrile (150 ml). 4,4′-Dimethoxytrityl chloride (DMTCl, 18.6 g, 55 mmol) was added. The mixture was stirred at room temperature for 30 min. and methanol (MeOH, 0.2 ml) was added. After 10 min., triethylamine (20 ml) and succinic anhydride (15 g) were added and the mixture was stirred overnight. The mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane (200 ml) and washed with triethylammonium phosphate (0.5 M, pH 7, 3×100 ml). The organic layer was dried (Na2SO4) and evaporated to approximately 100 ml. Hexane (150 ml) was added. The mixture was shaken for 5 min. and the supernatant was decanted. The residue was dried to give a yellow solid (36.8 g, 90%).

Aufarbeitung

  1. waitAfter 10 min.
  2. stirringthe mixture was stirred overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (200 ml)
  5. washwashed with triethylammonium phosphate (0.5 M, pH 7, 3×100 ml)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customevaporated to approximately 100 ml
  8. additionHexane (150 ml) was added
  9. stirringThe mixture was shaken for 5 min.
  10. customthe supernatant was decanted
  11. customThe residue was dried

Quellen und Nachweise

ORD-Eintrag
ord-31150971ef5548aca6bcf0ff9556428b
Quelldatensatz
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07002006B2

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