2-Cyanoethyl tetraisopropylphosphorodiamidite → Deoxyguanosine

HRID 635504

Reaktionsgleichung

Reaktionsgleichung von HRID 635504
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 135398592Deoxyguanosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c540f90c253c486fbbbc4a3f8e2d1e0b
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187914B1

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