Diisopropylethylamine → N2-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl) guanosine

HRID 1694676

Reaction equation

HRID 1694676 reaction equation
[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:46])[C:8]2[N:9]=[CH:10][N:11]([C:44]=2[N:45]=1)[C@@H:12]1[O:43][C@H:17]([CH2:18][O:19][C:20]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C@@H:15]([OH:16])[C@H:13]1[OH:14])(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:56]([CH2:58][CH2:59][O:60][CH2:61]Cl)#[N:57].C(=O)(O)[O-].[Na+]>ClCCCl>[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:46])[C:8]2[N:9]=[CH:10][N:11]([C:44]=2[N:45]=1)[C@@H:12]1[O:43][C@H:17]([CH2:18][O:19][C:20]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[C@@H:15]([OH:16])[C@H:13]1[O:14][CH2:61][O:60][CH2:59][CH2:58][C:56]#[N:57])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 116654052-Cyanoethyl chloromethyl etherHCID 136122477N-Acetyl-5'-DMTguanosine

Product 1

HCID 136387249N2-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl) guanosineYield 63.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N2-Acetyl-5′-O-(4,4′-dimethoxytrityl)guanosine (627 mg, 1 mmol) was dissolved in 4 mL of 1,2-dichloroethane, and 452 mg of diisopropylethylamine (3.5 mmol) was added, and then 365 mg of dibutylstannyl dichloride (1.2 mmol) was added. And then, the reaction solution was reacted at room temperature for 1 hour. Then, the reaction was performed at 80° C., and 155.4 mg of chloromethyl 2-cyanoethyl ether (1.3 mmol) was added dropwise, and the solution was stirred for 60 minutes. After the reaction completed, the reaction solution was mixed with an aqueous saturated sodium bicarbonate solution, and was subjected to extraction with methylene chloride. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The obtained mixture was purified by 30 g of silica gel column chromatography to obtain N2-acetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl) guanosine (450 mg, yield 63%).

Workup

  1. customAnd then, the reaction solution was reacted at room temperature for 1 hour
  2. customwas performed at 80° C.
  3. extractionwas subjected to extraction with methylene chloride
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe obtained mixture was purified by 30 g of silica gel column chromatography

Sources & evidence

ORD record
ord-fd7d1f7ef1304c92abc5b4f55a5e26f0
Source dataset
uspto-grants-2012_04
Patent number
US08158775B2

Linked notes

Loading…