Methanol → 6-N-(4-Monomethoxytrityl)-9-(3,5-di-O-benzoyl-2-deoxy-beta-L-threo-pentofuranosyl)adenine

HRID 496565Notes

Reaction equation

HRID 496565 reaction equation
[C:1]([O:9][C@@H:10]1[C@H:14]([CH2:15][O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:13][C@H:12]([N:25]2[CH:33]=[N:32][C:31]3[C:26]2=[N:27][CH:28]=[N:29][C:30]=3[NH2:34])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][O:36][C:37]1[CH:56]=[CH:55][C:40]([C:41](Cl)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:39][CH:38]=1.CO>N1C=CC=CC=1>[CH3:35][O:36][C:37]1[CH:56]=[CH:55][C:40]([C:41]([NH:34][C:30]2[N:29]=[CH:28][N:27]=[C:26]3[C:31]=2[N:32]=[CH:33][N:25]3[C@H:12]2[O:13][C@@H:14]([CH2:15][O:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:10]([O:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11]2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 84462p-(Chlorodiphenylmethyl)anisoleHCID 120709949-(3,5-Di-O-benzoyl-2-deoxy-beta-L-threo-pentofuranosyl)adenine

Product 1

HCID 120709956-N-(4-Monomethoxytrityl)-9-(3,5-di-O-benzoyl-2-deoxy-beta-L-threo-pentofuranosyl)adenineYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 4 (0.88 g, 1.92 mmol) in dry pyridine (40 mL) was added 4-monomethoxytrityl chloride (1.18 g, 3.84 mmol). The mixture was stirred at 60° C. for 24 h. After addition of methanol (5 mL), the solution was concentrated to dryness, the residue was dissolved in dichloromethane (50 mL) and washed successively with water (30 mL), aqueous saturated NaHCO3 (30 mL) and water (30 mL). The organic layer was dried, filtered, concentrated and co-evaporated with toluene to give pure 5 (1.01 g, 72%) as a foam: 1H NMR (CDCl3): δ 2.9-3.0 (m, 2H, H-2′ and H-2″), 3.62 (s, 3H, OCH3), 4.6-4.8 (m, 3H, H-4′, H-5′ and H5″), 5.85 (pt, 1H, H-3′), 6.44 (dd, 1H, H-1′, J1′,2′=3.1 Hz, J1′,2″=7.3 Hz), 6.9 (br s, 1H, NH-6), 6.7-6.8 and 7.2-7.4 (2m, 24H, 2 benzoyls and MMTr), 7.97 and 8.13 (2s, 2H, H-2 and H-8); ms: matrix G/T, (FAB+) m/z 732 [M+H]+, (FAB−) m/z 730 [M−H]−; UV (95% ethanol): λmax 274 nm (ε 12100), 225 nm (ε 24200), λmin 250 nm (ε 5900); [α]D20=−16 (c 1.12, DMSO).

Workup

  1. concentrationthe solution was concentrated to dryness
  2. dissolutionthe residue was dissolved in dichloromethane (50 mL)
  3. washwashed successively with water (30 mL), aqueous saturated NaHCO3 (30 mL) and water (30 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bc191f582c8f42368cca38d15852e9e7
Source dataset
uspto-grants-2005_09
Patent number
US06946450B2

Reaction notes

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