Acetic Acid → Uridine Tetraphosphate

HRID 551769

反応式

HRID 551769 の反応式
[OH:1][P:2]([O:5][P:6]([O:9][P:10]([O:13][P:14]([OH:17])([OH:16])=[O:15])([OH:12])=[O:11])([OH:8])=[O:7])(=[O:4])[OH:3].[Si]([O:25][C@@H:26]1[C@@H:30]([CH2:31][OH:32])[O:29][C@@H:28]([N:33]2[CH:40]=[CH:39][C:37](=[O:38])[NH:36][C:34]2=[O:35])[C@@H:27]1[OH:41])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.CC(O)=O.[SiH3]O[SiH3]>CC#N>[OH:17][P:14]([O:13][P:10]([O:9][P:6]([O:5][P:2]([OH:4])([OH:3])=[O:1])([OH:8])=[O:7])([OH:12])=[O:11])(=[O:15])[OH:16].[C@@H:28]1([N:33]2[CH:40]=[CH:39][C:37](=[O:38])[NH:36][C:34]2=[O:35])[O:29][C@H:30]([CH2:31][OH:32])[C@@H:26]([OH:25])[C@H:27]1[OH:41]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 123318DisiloxaneHCID 2724141Tetrabutylammonium FluorideHCID 131728787HCID 131728787、化合物

生成物 1

HCID 131728786Uridine Tetraphosphate収率 94%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

The 3′-O-TBDMS-Uridine Tetraphosphate [8] (2.55 mg, 0.00376 mmol) was taken up in CH3CN (Aldrich anhydrous, 160 μL). Tetrabutylammonium fluoride in THF (1.0 M, Aldrich, 113 μL, 0.113 mmol) and HOAc (glacial, Aldrich, 2.2 μL, 0.0376 mmol) were added to the solution. The resulting reaction mixture was allowed to stir for 21 hours at ambient temperature. HPLC analysis of the reaction at this time showed no remaining silyl ether. The volatile materials were removed on a rotary evaporator. The product mixture was resuspended in H2O, and the product was purified by reversed phase HPLC. (Column: Zorbax SB-C18, 9.4 mm×25 cm. Solvent A: 0.1 M TEAA, 2.5% CH3CN, pH=7.0; Solvent B: CH3CN. Flow rate: 4.0 mL/minute. Gradient: t=0 minutes, 100% A; t=15 minutes, 75% A/25% B; t=15.01 minutes, 100% B; t=20 minutes, 100% A; t=27 minutes, 100% A. Retention time: 7.05 minutes). The purified material was lyophilized. The resulting material was resuspended and lyophilized a total of 5 times to ensure complete removal of TEAA salts. Before the final lyophilization, the material was quantified by UV (2.00 mg, 94% yield). The compound [9] obtained in this manner was a white solid.

後処理

  1. customThe resulting reaction mixture
  2. customHPLC analysis of the reaction at this time
  3. customThe volatile materials were removed on a rotary evaporator
  4. customthe product was purified by reversed phase HPLC
  5. custom(Column: Zorbax SB-C18, 9.4 mm×25 cm. Solvent A: 0.1 M TEAA, 2.5% CH3CN, pH=7.0; Solvent B: CH3CN. Flow rate: 4.0 mL/minute. Gradient: t=0 minutes, 100% A; t=15 minutes, 75% A/25% B; t=15.01 minutes, 100% B; t=20 minutes, 100% A; t=27 minutes, 100% A. Retention time: 7.05 minutes)
  6. customremoval of TEAA salts

出典と根拠

ORDレコード
ord-ba476fec9ba74762b753ad476f57b461
出典データセット
uspto-grants-2011_05
特許番号
US07947817B2

関連ノート

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