Triphenylphosphine → (S)-2-[bis-(t-butoxycarbonyl)amino]-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurine

HRID 6269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 6269
[CH2:1]([O:8][CH2:9][C@@H:10]([CH2:21][OH:22])[O:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42]([O:46][C:47]([N:49]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[C:50]1[N:58]=[C:57]2[C:53]([N:54]=[CH:55][N:56]2O)=[C:52]([O:60][CH3:61])[N:51]=1)=[O:48])([CH3:45])([CH3:44])[CH3:43].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:65]([O:64][C:62]([N:49]([C:47]([O:46][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:48])[C:50]1[N:58]=[C:57]2[C:53]([N:54]=[CH:55][N:56]2[O:22][CH2:21][C@@H:10]([O:11][CH2:12][P:13]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:20])[CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:52]([O:60][CH3:61])[N:51]=1)=[O:63])([CH3:68])([CH3:67])[CH3:66]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 145239662-[Bis-(t-butoxycarbonyl)amino]-9-hydroxy-6-methoxypurineHCID 53890153diethyl (R)-[2-benzyloxy-1-(hydroxymethyl)ethoxy]methylphosphonate

Produkt 1

HCID 53696618(S)-2-[bis-(t-butoxycarbonyl)amino]-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurineAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of diethyl (R)-[2-benzyloxy-1-(hydroxymethyl)ethoxy]methylphosphonate (1.0 g, 3 mmol), triphenylphosphine (1.18 g, 4.5 mmol) and 2-[bis-(t-butoxycarbonyl)amino]-9-hydroxy-6-methoxypurine (1.15 g, 3 mmol) in dry THF (20 ml), cooled in ice and under a mitrogen atmosphere, was added, dropwise, diethyl azodicarboxylate (0.71 ml, 4.5 mmol). The resulting solution was allowed to warm to ambient temperature and left stirring for 16 hours. The solvent was evaporated under reduced pressure and the residue obtained chromatographed on silica gel using hexane/ethyl acetate 2:1 as eluant. The eluant was changed as follows: hexane/ethyl acetate 1:1, hexane/ethyl acetate 1:2 and finally to ethyl acetate to give (S)-2-[bis-(t-butoxycarbonyl)amino]-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurine as a colourless oil (1.85 g, 88%).

Aufarbeitung

  1. additionwas added
  2. waitleft
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue obtained
  5. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5bc3817b8fb84fdcb2e908b50be90647
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05247085

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