2-chloro-N6-(3-iodobenzyl)-9-[2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl]-adenine → 2-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol

HRID 965191

반응식

HRID 965191 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:33][C@H:32]([CH2:34][O:35]C(=O)C3C=CC=CC=3)[C@@H:22]([O:23]C(=O)C3C=CC=CC=3)[C@H:12]2[O:13]C(=O)C2C=CC=CC=2)=[C:4]([NH:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([I:52])[CH:47]=2)[N:3]=1.N.CO>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:33][C@H:32]([CH2:34][OH:35])[C@@H:22]([OH:23])[C@H:12]2[OH:13])=[C:4]([NH:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([I:52])[CH:47]=2)[N:3]=1

참가 물질

3

반응물 2

HCID 101019962-chloro-N6-(3-iodobenzyl)-9-[2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl]-adenineHCID 21705897Ammonia methanol

생성물 1

HCID 103465112-[2-Chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol수율 94%

실험 절차

A mixture of 2-chloro-N6 -(3-iodobenzyl)-9-[2,3,5-tri-O-benzoyl-β-D-ribofuranosyl]-adenine (760 mg, 0.916 mmol) and NH3 /MeOH (15 ml) was stirred for 66.5 h at room temperature. After the reaction mixture was concentrated to dryness, the residue was purified on a silica gel column chromatography (CHCl3 --MeOH, 20:1) to yield 2-chloro-N6 -(3-iodobenzyl)-9-[β-D-ribofuranosyl]-adenine (445 mg, 94%) as a foam. 1H NMR (DMSO-d6) d 3.55 (m, 1H, H-5'a), 3.65 (m, 1H, H-5'b), 3.94 (d, J=3.6 Hz, 1H, H-4'), 4.12 (m, 1H, H-3'), 4.51 (q, J=5.5 Hz, 1H, H-2'), 4.60 (br d, J=5.7 Hz, 2H, CH2), 5.04 (pseudo t, J=5.7 and 5.5 Hz, 1H, exchangeable with D2O, 5'-OH), 5.19 (d, J=4.9 Hz, 1H, exchangeable with D2O, OH), 5.47 (d, J=6.0 Hz, 1H, exchangeable with D2O, OH), 5.83 (d, J=5.5 Hz, 1H, H-1'), 7.13 (pseudo t, J=7.9 and 7.6 Hz, 1H, H-5"), 7.36 (d, J=7.5 Hz, 1H, H-4" or -6"), 7.60 (d, J=7.9 Hz, 1H, H-4" or -6"), 7.74 (s, 1H, H-2"), 8.43 (s, 1H, H-8), 8.94 (br t, J=6.0 Hz, 1H, exchangeable with D2O, NH,).

후처리

  1. concentrationAfter the reaction mixture was concentrated to dryness
  2. customthe residue was purified on a silica gel column chromatography (CHCl3 --MeOH, 20:1)

출처 및 근거

ORD 기록
ord-c63ebbb486d44958bd68a373619069f2
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773423

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