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

HRID 365945Notes

Reaction equation

HRID 365945 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

Compound 112 (5.59 g, 8.17 mmol) was dissolved in dry CH2Cl2 (40.42 mL). To this Na2O4 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 aldehyde 113 (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-7496d5cc33344a68b2dd1e391568ac93
Source dataset
uspto-grants-2000_10
Patent number
US06127533

Reaction notes

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