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

HRID 413102Notes

Reaction equation

HRID 413102 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 H-5″), 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):λmax274 nm (ε 12100), 225 nm (ε 24200), λmin250 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-8da2b10850284473a6e75e881f1638ba
Source dataset
uspto-grants-2003_05
Patent number
US06566344B1

Reaction notes

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