2-Cyanoethyl tetraisopropylphosphorodiamidite → Deoxyadenosine

HRID 635499

Reaction equation

HRID 635499 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 13730Deoxyadenosine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6625e8aedc394629bd66356b7ecbe40a
Source dataset
uspto-grants-2001_02
Patent number
US06187914B1

Linked notes

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