Triethylamine → 3'-O-allyl-5'-O-tert-butyldiphenylsilyl-N6-benzoyl-adenosine

HRID 636901Notes

Reaction equation

HRID 636901 reaction equation
[CH2:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][OH:11])[O:8][C@@H:7]([N:12]2[C:29]3[N:28]=[CH:27][N:26]=[C:16]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:15]=3[N:14]=[CH:13]2)[C@@H:6]1[OH:30])[CH:2]=[CH2:3].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(N(CC)CC)C.[Si:52](Cl)([C:65]([CH3:68])([CH3:67])[CH3:66])([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][Si:52]([C:65]([CH3:68])([CH3:67])[CH3:66])([C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[O:8][C@@H:7]([N:12]2[C:29]3[N:28]=[CH:27][N:26]=[C:16]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:15]=3[N:14]=[CH:13]2)[C@@H:6]1[OH:30])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14812Phosphorus oxide (P4O10)HCID 94078tert-ButyldiphenylchlorosilaneHCID 110478913'-O-allyl-N6-benzoyl Adenosine

Product 1

HCID 110828223'-O-allyl-5'-O-tert-butyldiphenylsilyl-N6-benzoyl-adenosineYield 49%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Compound 110 (11.17 g, 27.84 mmol) was dried over P2O5 under vacuum at 40° C., then dissolved in dry CH2Cl2 (56 mL, sure seal from Aldrich). 4-dimethylaminopyridine (0.34 g, 2.8 mmol), triethylamine (23.82 mL, 167 mmol) and t-butyldiphenylsilyl chloride were added. The reaction mixture was stirred vigorously for 12 hr. Reaction was monitored by TLC (ethyl acetate:hexane 1:1). It was then diluted with CH2Cl2 (50 mL) and washed with water (3×30 mL). Dichloromethane layer was dried over anhydrous Na2SO4 and evaporated to dryness. Residue purified by flash chromatography (ethyl acetate:hexane 1:1 as eluent) to get 111 as a white foam (8.85 g, 49%). Rf 0.35 (ethyl acetate:hexane, 1:1)

Workup

  1. customReaction
  2. washwashed with water (3×30 mL)
  3. dry with materialDichloromethane layer was dried over anhydrous Na2SO4
  4. customevaporated to dryness
  5. customResidue purified by flash chromatography (ethyl acetate:hexane 1:1 as eluent)

Sources & evidence

ORD record
ord-96d48e2286654d8995e9de40e551fc38
Source dataset
uspto-grants-2001_02
Patent number
US06194598B1

Reaction notes

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