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

HRID 6269노트

반응식

HRID 6269 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 53696618(S)-2-[bis-(t-butoxycarbonyl)amino]-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurine수율 88.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-5bc3817b8fb84fdcb2e908b50be90647
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05247085

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