2-Cyanoethyl tetraisopropylphosphorodiamidite → Deoxyguanosine

HRID 635504

반응식

HRID 635504 반응식
[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

참가 물질

6

반응물 4

HCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 21877088Acetonitrile methylene chlorideHCID 1371829655'-O-p-Nitrobenzoyl-2-N-t-ButylphenoxyacetyldeoxyguanosineHCID 178458033HCID 178458033, 화합물

생성물 1

HCID 135398592Deoxyguanosine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c540f90c253c486fbbbc4a3f8e2d1e0b
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187914B1

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