p-Toluenesulfonic acid → N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-5-O-tert-butyldimethylsilyl-3-O-tetrahydropyranyl-beta-D-erythro-pentofuranosyl]-guanine

HRID 552086Notes

Reaction equation

HRID 552086 reaction equation
[CH3:1][O:2][N:3]([C:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:4]1[NH:5][C:6](=[O:31])[C:7]2[N:8]=[CH:9][N:10]([C@@H:13]3[O:18][C@H:17]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C@@H:15]([OH:16])[C@@:14]3([C:29]#[CH:30])[F:28])[C:11]=2[N:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:62]1[CH:67]=[CH:66][CH2:65][CH2:64][CH2:63]1>C1COCC1.C(Cl)Cl>[CH3:1][O:2][N:3]([C:32]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:4]1[NH:5][C:6](=[O:31])[C:7]2[N:8]=[CH:9][N:10]([C@@H:13]3[O:18][C@H:17]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:25])[CH3:26])([CH3:22])[CH3:23])[C@@H:15]([O:16][CH:63]4[CH2:64][CH2:65][CH2:66][CH2:67][O:62]4)[C@@:14]3([C:29]#[CH:30])[F:28])[C:11]=2[N:12]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 137227857N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-5-O-tert-butyldimethylsilyl-beta-D-erythro-pentofuranosyl]guanine

Product 1

HCID 137227859N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-5-O-tert-butyldimethylsilyl-3-O-tetrahydropyranyl-beta-D-erythro-pentofuranosyl]-guanine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 13 (0.8 mmol), in anh THF (20 ml/mmol), at room temperature, was added p-toluen sulfonic acid (0.12 mmol) and dihydropyran (2 ml/mmol). The reaction mixture was stirred at room temperature for 3 days and neutralized with TEA. The mixture was diluted with DCM, washed twice with H2O. The organic phase was dried over Na2SO4, filtered and evaporated. The crude material was purified by silica gel chromatography (DCM/MeOH) to yield the title compound. Molecular Formula C43H52FN5O6Si. Scan ES+ 780 (M+H)+

Workup

  1. washwashed twice with H2O
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by silica gel chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-77ae62ea5a2740bca26f3cdfc2c3104b
Source dataset
uspto-grants-2011_05
Patent number
US07951789B2

Reaction notes

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