tert-Butyldimethylsilyl chloride → N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-5-O-tert-butyldimethylsilyl-beta-D-erythro-pentofuranosyl]guanine

HRID 552083Notes

Reaction equation

HRID 552083 reaction equation
[CH3:1][O:2][N:3]([C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:4]1[NH:5][C:6](=[O:24])[C:7]2[N:8]=[CH:9][N:10]([C@@H:13]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@@:14]3([C:22]#[CH:23])[F:21])[C:11]=2[N:12]=1.[Si:44](Cl)([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45]>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][O:2][N:3]([C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:4]1[NH:5][C:6](=[O:24])[C:7]2[N:8]=[CH:9][N:10]([C@@H:13]3[O:18][C@H:17]([CH2:19][O:20][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[C@@H:15]([OH:16])[C@@:14]3([C:22]#[CH:23])[F:21])[C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 136343925N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-beta-D-erythro-pentofuranosyl]guanine

Product 1

HCID 137227857N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-5-O-tert-butyldimethylsilyl-beta-D-erythro-pentofuranosyl]guanine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 12 (2.29 mmol) in pyridine (5 ml) at 0° C., was added tert-butyldimethylsilyl chloride (2.75 mmol). The reaction mixture was stirred at room temperature for 24 hours. It was then diluted in DCM and washed twice with H2O. The organic phase was extracted, dried over Na2SO4, filtered and evaporated. The crude material was purified by silica gel chromatography (DCM/MeOH) to yield the title compound. Yellowish oil. Molecular Formula C38H44 FN5O5Si. Scan ES+ 696 (M+H)+, λmax 260 nm. Scan ES− 694 (M+H)−, UV λmax 260 nm

Workup

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

Sources & evidence

ORD record
ord-5c829bba926341e89fd7ef5e6de66699
Source dataset
uspto-grants-2011_05
Patent number
US07951789B2

Reaction notes

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