ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Ammonium Hydroxide → 5-methylseleno-3'-t-butyldimethylsilyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxycytidine

HRID 2406285
ノート
印刷プレビュー

反応式

HRID 2406285 の反応式
[CH3:1][Se:2][C:3]1[C:4](=O)[NH:5][C:6](=[O:47])[N:7]([CH:46]=1)[C@@H:8]1[O:38][C@H:12]([CH2:13][O:14][C:15]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:24][CH3:25])([O:22][CH3:23])[CH2:18][CH:17]=2)[C@@:10]([Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])([OH:11])[CH2:9]1.C([N:52](C(C)C)CC)(C)C.C(C1C=CC(S(Cl)(=O)=O)=C(C(C)C)C=1C(C)C)(C)C.[OH-].[NH4+]>C(#N)C.CN(C)C1C=CN=CC=1.C(Cl)Cl.CO.C(OCC)(=O)C.CCCCCC>[CH3:1][Se:2][C:3]1[C:4]([NH2:52])=[N:5][C:6](=[O:47])[N:7]([CH:46]=1)[C@@H:8]1[O:38][C@H:12]([CH2:13][O:14][C:15]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])([O:24][CH3:25])[CH2:18][CH:17]=2)[C@@:10]([Si:39]([C:42]([CH3:43])([CH3:45])[CH3:44])([CH3:40])[CH3:41])([OH:11])[CH2:9]1
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 11514985Triisopropylbenzenesulfonyl chlorideHCID 1317317735-methylseleno-3'-t-butyldimethylsilyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxyuridine

生成物 1

HCID 1317317725-methylseleno-3'-t-butyldimethylsilyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxycytidine収率 64.9%

試薬・触媒・溶媒 5

HCID 142844-(Dimethylamino)pyridine触媒HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

After 5-methylseleno-3′-t-butyldimethylsilyl-5′-O-(4,4-dimethoxytrityl)-2′-deoxyuridine 480 mg (MW 752.2, 0.64 mmol) was dissolved in acetonitrile 10 ml, diisopropylethyl amine (0.67 ml, 3.19 mmol, 5 eq.), triisopropylbenzenesulfonyl chloride (576 mg, 1.59 mmol, 2.5 eq.) and p-dimethylamino pyridine (96 mg, 0.64 mmol, 1 eq.) were added sequentially. The reaction mixture was stirred for 16 hours and monitored on TLC (ethyl acetate/hexane, 3:7). After completion, excessive concentrated ammonium hydroxide solution was added dropwise and the reaction was stirred under room temperature for 1 hour. After the reaction was completed (monitored on TLC, 5% MeOH in CH2Cl2, Rf=5), the organic solvent and ammonium hydroxide were evaporated under reduced pressure. A silica gel column was equilibrated with CH2Cl2 before the crude product was loaded and purified on the column. The product was eluded by MeOH in CH2Cl2 (1-7%). The fractions containing the product were combined, evaporated and dried on high vacuum overnight to yield yellow solid 307 mg. (yield=64%). 1H-NMR (400 MHz, DMSO) δ: 0.05 (s, 6H, SiCH3), 0.87 (s, 9H, t-butyl), 1.95 (s, 3H, SeCH3), 2.18-2.25 and 2.58-2.62 (2×m, 2H, H-2′), 3.30-3.33 and 3.46-3.49 (2×m, 2H, H-5′), 3.84 (s, 6H, 2×OMe), 4.03-4.08 (m, 1H, H-3′), 4.42-4.46 (m, 1H, H-4′), 6.11 (s, 1H, NH2), 6.28-631 (t, J=5.6 Hz, 1H, H-1′), 6.50 (s, 1H, NH2), 6.86-7.48 (m, 13H, arom-H), 8.30 (s, 1H, H-6). 13C NMR (100 MHz, DMSO) δ: −4.86 and −4.69 [Si(CH3)2], 7.31 (SeCH3), 17.96 [SiC(CH3)], 25.74 [SiC(CH3)], 41.74 (C-2′), 55.26 (OMe), 62.88 (C-5′), 72.23 (C-3′), 85.55 (C-4′), 87.05 (arom-C), 87.16 (C-1′), 103.45 (C-5), 113.23 (arom-C), 126.94 Carom-C), 128.15 (arom-C), 130.11 (arom-C), 135.50 (arom-C), 141.74 (C-6), 144.41 (arom-C), 149.89 (C-2), 155.46 (arom-C), 158.66 (C-4), 161.46 (arom-C), 165.55 (arom-C). HR-MS (ESI-TOF, positive ion mode): molecular formula, C32H47N3O6SeSi: [M+H]−: 738.2468 (calc. 738.2478).

後処理

  1. stirringthe reaction was stirred under room temperature for 1 hour
  2. customthe organic solvent and ammonium hydroxide were evaporated under reduced pressure
  3. custompurified on the column
  4. additionThe fractions containing the product
  5. customevaporated
  6. customdried on high vacuum overnight

出典と根拠

ORDレコード
ord-369b37c9c2e34c3fb2a1b88155b460f8
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08809357B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート