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Methanol → Triethylammonium 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methyluridine-3'-O-succinate

HRID 891222
ノート
印刷プレビュー

反応式

HRID 891222 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C@@H:6]1[C@H:10]([OH:11])[C@@H:9]([CH2:12][OH:13])[O:8][C@H:7]1[N:14]1[CH:21]=[C:20]([CH3:22])[C:18](=[O:19])[NH:17][C:15]1=[O:16].[CH3:23][O:24][C:25]1[CH:46]=[CH:45][C:28]([C:29](Cl)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:27][CH:26]=1.C[OH:48].[C:49]1(=[O:55])[O:54][C:52](=[O:53])[CH2:51][CH2:50]1>N1C(C)=CC=CC=1C.C(#N)C.C(N(CC)CC)C>[CH3:23][O:24][C:25]1[CH:46]=[CH:45][C:28]([C:29]([O:13][CH2:12][C@H:9]2[O:8][C@@H:7]([N:14]3[CH:21]=[C:20]([CH3:22])[C:18](=[O:19])[NH:17][C:15]3=[O:16])[C@H:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[C@@H:10]2[O:11][CH:51]([C:52]([O-:48])=[O:53])[CH2:50][C:49]([O-:54])=[O:55])([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:27][CH:26]=1.[CH2:21]([NH+:14]([CH2:7][CH3:6])[CH2:15][CH3:23])[CH3:20].[CH2:21]([NH+:14]([CH2:7][CH3:6])[CH2:15][CH3:23])[CH3:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 887MethanolHCID 7922Succinic anhydrideHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 112439882'-O-(2-Methoxyethyl)-5-methyl-uridine

生成物 1

HCID 86593945Triethylammonium 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methyluridine-3'-O-succinate収率 90%

試薬・触媒・溶媒

3
HCID 6342Acetonitrile溶媒HCID 79372,6-Lutidine溶媒HCID 8471Triethylamine溶媒

実験手順

2′-O-(2-methoxyethyl)-5-methyluridine (MOE T, 15.8 g, 50 mmol) was dissolved in 2,6-lutidine (23.3 ml) and acetonitrile (150 ml). 4,4′-Dimethoxytrityl chloride (DMTCl, 18.6 g, 55 mmol) was added. The mixture was stirred at room temperature for 30 min. and methanol (MeOH, 0.2 ml) was added. After 10 min., triethylamine (20 ml) and succinic anhydride (15 g) were added and the mixture was stirred overnight. The mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane (200 ml) and washed with triethylammonium phosphate (0.5 M, pH 7, 3×100 ml). The organic layer was dried (Na2SO4) and evaporated to approximately 100 ml. Hexane (150 ml) was added. The mixture was shaken for 5 min. and the supernatant was decanted. The residue was dried to give a yellow solid (36.8 g, 90%).

後処理

  1. waitAfter 10 min.
  2. stirringthe mixture was stirred overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (200 ml)
  5. washwashed with triethylammonium phosphate (0.5 M, pH 7, 3×100 ml)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customevaporated to approximately 100 ml
  8. additionHexane (150 ml) was added
  9. stirringThe mixture was shaken for 5 min.
  10. customthe supernatant was decanted
  11. customThe residue was dried

出典と根拠

ORDレコード
ord-31150971ef5548aca6bcf0ff9556428b
出典データセット
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07002006B2

反応ノート

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