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Methanol → 6-N-(4-Monomethoxytrityl)-9-(3,5-di-O-benzoyl-2-deoxy-beta-L-threo-pentofuranosyl)adenine

HRID 413102
ノート
印刷プレビュー

反応式

HRID 413102 の反応式
[C:1]([O:9][C@@H:10]1[C@H:14]([CH2:15][O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:13][C@H:12]([N:25]2[CH:33]=[N:32][C:31]3[C:26]2=[N:27][CH:28]=[N:29][C:30]=3[NH2:34])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][O:36][C:37]1[CH:56]=[CH:55][C:40]([C:41](Cl)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:39][CH:38]=1.CO>N1C=CC=CC=1>[CH3:35][O:36][C:37]1[CH:56]=[CH:55][C:40]([C:41]([NH:34][C:30]2[N:29]=[CH:28][N:27]=[C:26]3[C:31]=2[N:32]=[CH:33][N:25]3[C@H:12]2[O:13][C@@H:14]([CH2:15][O:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:10]([O:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11]2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:39][CH:38]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 887MethanolHCID 84462p-(Chlorodiphenylmethyl)anisoleHCID 120709949-(3,5-Di-O-benzoyl-2-deoxy-beta-L-threo-pentofuranosyl)adenine

生成物 1

HCID 120709956-N-(4-Monomethoxytrityl)-9-(3,5-di-O-benzoyl-2-deoxy-beta-L-threo-pentofuranosyl)adenine収率 72%

試薬・触媒・溶媒 1

HCID 1049Pyridine
溶媒

反応条件

温度
60 °C

実験手順

To a solution of compound 4 (0.88 g, 1.92 mmol) in dry pyridine (40 mL) was added 4-monomethoxytrityl chloride (1.18 g, 3.84 mmol). The mixture was stirred at 60° C. for 24 h. After addition of methanol (5 mL), the solution was concentrated to dryness, the residue was dissolved in dichloromethane (50 mL) and washed successively with water (30 mL), aqueous saturated NaHCO3 (30 mL) and water (30 mL). The organic layer was dried, filtered, concentrated and co-evaporated with toluene to give pure 5 (1.01 g, 72%) as a foam: 1H NMR (CDCl3):δ 2.9-3.0 (m, 2H, H-2′ and H-2″), 3.62 (s, 3H, OCH3), 4.6-4.8 (m, 3H, H-4′, H-5′ and H-5″), 5.85 (pt, 1H, H-3′), 6.44 (dd, 1H, H-1′, J1′,2′,=3.1 Hz, J1′,2″=7.3 Hz), 6.9 (br s, 1H, NH-6), 6.7-6.8 and 7.2-7.4 (2m, 24H, 2 benzoyls and MMTr), 7.97 and 8.13 (2s, 2H, H-2 and H-8); ms : matrix G/T, (FAB+) m/z 732 [M+H]+, (FAB−) m/z 730 [M-H]-; UV (95% ethanol):λmax274 nm (ε 12100), 225 nm (ε 24200), λmin250 nm (ε 5900); [α]D20=16 (c 1.12, DMSO).

後処理

  1. concentrationthe solution was concentrated to dryness
  2. dissolutionthe residue was dissolved in dichloromethane (50 mL)
  3. washwashed successively with water (30 mL), aqueous saturated NaHCO3 (30 mL) and water (30 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-8da2b10850284473a6e75e881f1638ba
出典データセット
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06566344B1

反応ノート

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