2-Cyanoethyl tetraisopropylphosphorodiamidite → Deoxyguanosine

HRID 635504

反応式

HRID 635504 の反応式
[N+](C1C=CC(C([O:10][CH2:11][C@H:12]2[O:16][C@@:15](C(=O)COC3C=CC=CC=3)([N:17]3[C:31]4[N:30]=[C:24]([NH:25]C(C)(C)C)[NH:23][C:21](=[O:22])[C:20]=4[N:19]=[CH:18]3)[CH2:14][C@@H:13]2[OH:42])=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:31]3[N:30]=[C:24]([NH2:25])[NH:23][C:21](=[O:22])[C:20]=3[N:19]=[CH:18]2)[O:16][C@H:12]([CH2:11][OH:10])[C@@H:13]([OH:42])[CH2:14]1

参加物

6

反応物 4

HCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 21877088Acetonitrile methylene chlorideHCID 1371829655'-O-p-Nitrobenzoyl-2-N-t-ButylphenoxyacetyldeoxyguanosineHCID 178458033HCID 178458033、化合物

生成物 1

HCID 135398592Deoxyguanosine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5′-O-p-nitrobenzoyl-2-N-t-butylphenoxyacetyldeoxyguanosine (1 eq) is dried in a dichloromethane/acetonitrile mixture and reacted with 1.2 eq of bisdiisopropylaminocyanoethoxyphosphine and 0.5 eq of diisopropylammoniumtetrazolide 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 redissolution in chloroform and 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 redissolution in chloroform and precipitation in hexane
  5. customthe product is dried under vacuum

出典と根拠

ORDレコード
ord-c540f90c253c486fbbbc4a3f8e2d1e0b
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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