Hydrochloric Acid → 9-(3,5-Di-O-benzyl-4-C-hydroxymethyl-beta-D-ribofuranosyl)-6-N-benzoyladenine

HRID 1007605노트

반응식

HRID 1007605 반응식
C([O:4][C@@H:5]1[C@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@:8]([CH2:27][O:28]C(=O)C)([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:7][C@H:6]1[N:32]1[CH:40]=[N:39][C:38]2[C:33]1=[N:34][CH:35]=[N:36][C:37]=2[NH:41][C:42](=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=O)C.C[O-].[Na+].Cl>CO>[CH2:11]([O:10][C@@H:9]1[C@@:8]([CH2:27][OH:28])([CH2:18][O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:7][C@@H:6]([N:32]2[CH:40]=[N:39][C:38]3[C:33]2=[N:34][CH:35]=[N:36][C:37]=3[NH:41][C:42](=[O:49])[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C@@H:5]1[OH:4])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 206107969-(2-O-Acetyl-4-C-acetyloxymethyl-3,5-di-O-benzyl-beta-D-ribofuranosyl)-6-N-benzoyl-adenine

생성물 1

HCID 206107979-(3,5-Di-O-benzyl-4-C-hydroxymethyl-beta-D-ribofuranosyl)-6-N-benzoyladenine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of nucleoside 58 (4.18 g, 6.28 mmol) in methanol (50 cm3) was added sodium methoxide (0.75 g, 13.8 mmol) at 0° C. The reaction mixture was stirred for 2 h, and ice was added. The mixture was neutralised using a 20% aqueous solution of HCl. Extraction was performed using dichloromethane (3×75 cm3), the organic phase was separated, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (98.5:1.5, v/v) as eluent to give nucleoside 59 as a white solid material (2.68 g, 73%). δH (CDCl3) 9.42 (1H, br s, NH), 8.58 (1H, s, H-8), 8.16 (1H, s, 2-H), 7.96 (2H, d, J 7.2, Bz), 7.52-7.08 (13H, m, Bn, Bz), 6.18 (1H, d, J 2.5, 1′-H), 4.85-4.38 (4H, m, Bn, 2′-H, 3′-H), 4.33 (2H, s, Bn) 3.90 (1H, d, J 11.9, 1″-Ha), 3.71 (1H, d, J 11.8, 1″-Hb), 3.50-3.39 (2H, m, 5-H). δC (CDCl3) 164.98 (NHCO), 152.19 (C-6), 151.00 (C-2), 149.34 (C-4), 142.28 (C-8), 137.32, 137.25, 133.46, 132.70, 128.69, 128.49, 128.40, 128.11, 128.03, 127.94, 127.83, 127.62, (Bz, Bn), 122.92 (C-5), 90.94, 88.75 (C-1′, C-4′), 77.65, 74.08, 73.44, 73.20, 71.12, 62.39 (C-1″, C-5′, C-2′, C-3′, 2×Bn). FAB-MS m/z 582 [M+H]+. Found: C, 65.6; H, 5.5; N, 11.7. C32H31N5O6 requires C, 66.1; H, 5.4; N, 12.0%.

후처리

  1. additionice was added
  2. extractionExtraction
  3. customthe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-5e73cead06574568b6ce8dff5ef7c8fc
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794499B2

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