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

HRID 928702Notes

Reaction equation

HRID 928702 reaction equation
[CH3:1][O:2][C:3]1[CH:55]=[CH:54][C:6]([C:7]([NH:20][C:21]2[N:29]=[CH:28][N:27]=[C:26]3[C:22]=2[N:23]=[CH:24][N:25]3[C@H:30]2[O:43][C@@H:42]([CH2:44][O:45]C(=O)C3C=CC=CC=3)[C@@H:32]([O:33]C(=O)C3C=CC=CC=3)[CH2:31]2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1>N>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:20][C:21]2[N:29]=[CH:28][N:27]=[C:26]3[C:22]=2[N:23]=[CH:24][N:25]3[C@H:30]2[O:43][C@@H:42]([CH2:44][OH:45])[C@@H:32]([OH:33])[CH2:31]2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:54][CH:55]=1

Participants

3

Reactant 1

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

Product 1

HCID 120709966-N-(4-Monomethoxytrityl)-9-(2-deoxy-beta-L-threo-pentofuranosyl)adenineYield 98.4%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

Compound 5 (0.95 g, 1.30 mmol) was treated with a solution (saturated at −10° C.) of methanolic ammonia (40 mL), at room temperature overnight. After concentration, the residue was dissolved in dichloromethane (60 mL) and washed with water (30 mL). The aqueous layer was extracted twice with dichloromethane (10 mL). The combined organic layer was dried, filtered and concentrated. The residue was purified by silica gel column chromatography (0-5% MeOH in dichloromethane) to give pure 6 (0.67 g, 98%) as a foam: 1H NMR (CDCl3): δ 2.6-2.9 (m, 2H, H-2′ and H-2″), 3.5 (br s, 1H, OH-5′), 3.55 (s, 3H, OCH3), 3.9-4.0 (m, 3H, H-4′, H-5′ and H-5″), 4.5-4.6 (m, 1H, H-3′), 6.03 (dd, 1H, H-1′, J1′,2′=4.0 Hz, J1′,2″=8.8 Hz), 7.0 (br s, 1H, NH-6), 6.7-6.8 and 7.1-7.4 (2m, 14H, MMTr), 7.40 (d, 1H, OH-3′, JH,OH=10.6 Hz), 7.80 and 7.99 (2s, 2H, H-2 and H-8); ms: matrix G/T, (FAB+) m/z 524 [M+H]+, 408 [BH2]+, (FAB−) m/z 1045 [2M−H]−, 522 [M−H]−, 406 [B]−; UV (95% ethanol): λmax 275 nm (ε 12300), λmin 247 nm (ε 3600); [α]D20=+28 (c 0.94, DMSO).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in dichloromethane (60 mL)
  3. washwashed with water (30 mL)
  4. extractionThe aqueous layer was extracted twice with dichloromethane (10 mL)
  5. customThe combined organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (0-5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-53b804541891465f8e22ee79fd4160a4
Source dataset
uspto-grants-2016_03
Patent number
US09290533B2

Reaction notes

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