6-N-(4-Monomethoxytrityl)-9-(3-O-benzoyl-2-deoxy-5-O-(4-mono-methoxytrityl)-beta-L-erythro-pentofuranosyl)adenine → 6-N-(4-Monomethoxytrityl)-9-(2-deoxy-5-O-(4-monomethoxytrityl)-beta-L-erythropentofuranosyl)adenine

HRID 968504Notes

Reaction equation

HRID 968504 reaction equation
[CH3:1][O:2][C:3]1[CH:68]=[CH:67][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:46]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=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][O:45][C:46]([C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)([C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[C:47]3[CH:48]=[CH:49][C:50]([O:53][CH3:54])=[CH:51][CH:52]=3)[C@H:32]([OH:33])[CH2:31]2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:67][CH:68]=1

Participants

3

Reactant 1

HCID 120709986-N-(4-Monomethoxytrityl)-9-(3-O-benzoyl-2-deoxy-5-O-(4-mono-methoxytrityl)-beta-L-erythro-pentofuranosyl)adenine

Product 1

HCID 120709996-N-(4-Monomethoxytrityl)-9-(2-deoxy-5-O-(4-monomethoxytrityl)-beta-L-erythropentofuranosyl)adenineYield 76%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

Compound 8 was treated by a solution (saturated at −10° C.) of methanolic ammonia (20 mL), at room temperature for 24 h, then the reaction mixture was concentrated to dryness. The residue was dissolved in dichloromethane (30 mL) and washed with water (20 mL). The aqueous layer was extracted by dichloromethane (2×20 mL) and the combined organic phase was dried, filtered and concentrated. Pure compound 9 (0.50 g, 76% from 7) was obtained as a foam after purification by silica gel column chromatography (0-2% MeOH in dichloromethane): 1H NMR (DMSO-d6): δ 2.2-2.3 (m, 1H, H-2′), 2.8-2.9 (m, 1H, H-2″), 3.1-3.2 (m, 2H, H-5′ and H-5″), 3.64 and 3.65 (2s, 6H, 2×OCH3), 3.97 (pq, 1H, H-4′), 4.4-4.5 (m, 1H, H-3′), 5.36 (d, 1H, OH-3′, JH,OH=4.5 Hz), 6.34 (t, 1H, H-1′, J1′,2′=J1′,2″=6.4 Hz), 6.8-6.9 and 7.1-7.4 (2m, 29H, 2 MMTr and NH-6), 7.81 and 8.32 (2s, 2H, H-2 and H-8); ms: matrix G/T, (FAB+) m/z 796 [M+H]+, 408 [BH2]+, (FAB−) m/z 794 [M−H]−, 406 [B]−; UV (95% ethanol): λmax 276 nm (ε 42600), λmin 248 nm (ε 23300); [α]D20=+29 (c 1.05, DMSO).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. dissolutionThe residue was dissolved in dichloromethane (30 mL)
  3. washwashed with water (20 mL)
  4. extractionThe aqueous layer was extracted by dichloromethane (2×20 mL)
  5. customthe combined organic phase was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-362ffacf413246339659015069b1a56f
Source dataset
uspto-grants-2007_12
Patent number
US07304043B2

Reaction notes

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