2-Cyanoethyl tetraisopropylphosphorodiamidite → Deoxyadenosine

HRID 635499

반응식

HRID 635499 반응식
[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

참가 물질

6

반응물 4

HCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 153826945'-o-p-Nitrobenzoyl-6-n-phenoxyacetyldeoxyadenosineHCID 21877088Acetonitrile methylene chlorideHCID 178458033HCID 178458033, 화합물

생성물 1

HCID 13730Deoxyadenosine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

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 precipitation in hexane
  5. customthe product is dried under vacuum

출처 및 근거

ORD 기록
ord-6625e8aedc394629bd66356b7ecbe40a
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187914B1

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