Methanol → 5'-O-tert-butyldiphenylsilyl-N6-benzoyl-2'-O-(formylmethyl)-adenosine

HRID 2229877Notes

Reaction equation

HRID 2229877 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[C:42]3[N:41]=[CH:40][N:39]=[C:29]([NH:30][C:31](=[O:38])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:28]=3[N:27]=[CH:26]2)[C@H:22]([O:43][CH2:44][CH:45]([OH:48])CO)[C@@H:21]1[OH:49])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C(Cl)Cl>[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[C:42]3[N:41]=[CH:40][N:39]=[C:29]([NH:30][C:31](=[O:38])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:28]=3[N:27]=[CH:26]2)[C@H:22]([O:43][CH2:44][CH:45]=[O:48])[C@@H:21]1[OH:49])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 572917365'-O-tert-butyldiphenylsilyl-N6-benzoyl-2'-O-(2,3-dihydroxypropyl)-adenosine

Product 1

HCID 536644125'-O-tert-butyldiphenylsilyl-N6-benzoyl-2'-O-(formylmethyl)-adenosineYield 105.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5′-O-tert-butyldiphenylsilyl-N6-benzoyl-2′-O-(2,3-dihydroxypropyl)-adenosine (5.59 g, 8.17 mmol) was dissolved in dry CH2Cl2 (40.42 mL). To this NaIO4 adsorbed on silica gel (Ref. J. Org. Chem. 1997, 62, 2622-2624) (16.34 g, 2 g/mmol) was added and stirred at ambient temperature for 30 minutes. Reaction monitored by TLC (5% MeOH in CH2Cl2). Reaction mixture was filtered and the filtrate washed thoroughly with CH2Cl2. Dichloromethane layer evaporated to get the title compound (5.60 g) that was used in the next step without purification. Rf 0.3 (5% MeOH in CH2Cl2).

Workup

  1. additionwas added
  2. customReaction
  3. customReaction mixture
  4. filtrationwas filtered
  5. washthe filtrate washed thoroughly with CH2Cl2
  6. customDichloromethane layer evaporated

Sources & evidence

ORD record
ord-07b4c202a8c14b90bddf72dee43432a0
Source dataset
uspto-grants-2002_07
Patent number
US06420549B1

Reaction notes

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