2-Cyanoethyl tetraisopropylphosphorodiamidite → Deoxyadenosine

HRID 635499

反応式

HRID 635499 の反応式
[N+](C1C=CC(C([O:10][CH2:11][C@H:12]2[O:16][C@@H:15]([N:17]3[C:36]4[N:35]=[CH:34][N:33]=[C:21]([NH:22]C(=O)COC5C=CC=CC=5)[C:20]=4[N:19]=[CH:18]3)[CH2:14][C@@H:13]2[OH:37])=O)=CC=1)([O-])=O.ClCCl.C(#N)C.C(N(P(N(C(C)C)C(C)C)OCCC#N)C(C)C)(C)C.N1[C-]=NN=N1.C([NH2+]C(C)C)(C)C>ClCCl>[C@@H:15]1([N:17]2[C:36]3[N:35]=[CH:34][N:33]=[C:21]([NH2:22])[C:20]=3[N:19]=[CH:18]2)[O:16][C@H:12]([CH2:11][OH:10])[C@@H:13]([OH:37])[CH2:14]1

参加物

6

反応物 4

HCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 153826945'-o-p-Nitrobenzoyl-6-n-phenoxyacetyldeoxyadenosineHCID 21877088Acetonitrile methylene chlorideHCID 178458033HCID 178458033、化合物

生成物 1

HCID 13730Deoxyadenosine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5′-O-p-Nitrobenzoyl-6-N-phenoxyacetyldeoxyadenosine (1 eq) is dried in a dichloromethane/acetonitrile mixture and reacted with 1.2 eq of bisdiisopropylaminocyanoethoxyphosphine and 0.5 eq of diisopropylammonium tetrazolide in anhydrous dichloromethane. After reacting for 2 hours, the reaction mixture is diluted and washed successively with 0.5 M sodium bicarbonate and saturated sodium chloride. The organic phase is evaporated to dryness. After precipitation in hexane, the product is dried under vacuum and stored under argon. This amidite is soluble in acetonitrile, a solvent in which oligonucleotide syntheses are conventionally carried out.

後処理

  1. additionthe reaction mixture is diluted
  2. washwashed successively with 0.5 M sodium bicarbonate and saturated sodium chloride
  3. customThe organic phase is evaporated to dryness
  4. customAfter precipitation in hexane
  5. customthe product is dried under vacuum

出典と根拠

ORDレコード
ord-6625e8aedc394629bd66356b7ecbe40a
出典データセット
uspto-grants-2001_02
特許番号
US06187914B1

関連ノート

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