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 1937370Notes

Reaction equation

HRID 1937370 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): δ2.6-2.9 (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-7d7b5cb607bb4fc29dafb7588bcf2d70
Source dataset
uspto-grants-2002_05
Patent number
US06395716B1

Reaction notes

Loading…