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Benzoyl chloride → 4-N-benzoyl-5-methylseleno-3'-t-butyldimethylsilyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxycytidine

HRID 2406286
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2406286
[CH3:1][Se:2][C:3]1[C:4]([NH2:48])=[N:5][C:6](=[O:47])[N:7]([CH:46]=1)[C@@H:8]1[O:38][C@H:12]([CH2:13][O:14][C:15]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:24][CH3:25])([O:22][CH3:23])[CH2:18][CH:17]=2)[C@@:10]([Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])([OH:11])[CH2:9]1.[C:49](Cl)(=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.C(OCC)(=O)C>CCCCCC>[C:49]([NH:48][C:4]1[C:3]([Se:2][CH3:1])=[CH:46][N:7]([C@@H:8]2[O:38][C@H:12]([CH2:13][O:14][C:15]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])([O:24][CH3:25])[CH2:20][CH:21]=3)[C@@:10]([Si:39]([C:42]([CH3:43])([CH3:44])[CH3:45])([CH3:40])[CH3:41])([OH:11])[CH2:9]2)[C:6](=[O:47])[N:5]=1)(=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1
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Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 1317317725-methylseleno-3'-t-butyldimethylsilyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxycytidine2×

Produkt 1

HCID 1317317744-N-benzoyl-5-methylseleno-3'-t-butyldimethylsilyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxycytidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058
Hexane
Lösungsmittel

Versuchsvorschrift

5-methylseleno-3′-t-butyldimethylsilyl-5′-O-(4,4-dimethoxytrityl)-2′-deoxycytidine (compound 2) 300 mg (MW 751.3, 0.4 mmol) was placed in a flask and dried on high vacuum for one hour before addition of anhydrous pyridine 10 ml. Benzoyl chloride 0.03 ml (0.6 mmol, 1.5 eq.) was added dropwise before the reaction solution was stirred for 1 hour. After the reaction was completed (monitored on TLC, 30% ethyl acetate in hexane, Rf=0.5), the crude product was extracted with saturated NaCl solution and ethyl acetate. The organic phase was removed and aqueous phase was extracted with ethyl acetate three times. The combined organic phase was dried over anhydrous MgSO4, the salt was filtered, and the organic solvents were evaporated under reduced pressure. The residue was purified on a silica gel column (equilibrated with hexane) and eluted with an ethyl acetate/hexane gradient (EtOAc in hexane, 10-50%). Compound 3 was isolated and dried to afford a yellow-green solid 287 mg. (yield=84%). 1H-NMR (400 MHz, DMSO) δ: 0.09 and 0.04 [2×s, 6H, Si(CH3)2], 0.86 (s, 9H, t-butyl), 2.02 (s, 3H, SeCH3), 2.18-2.20 and 2.43-2.52 (2×m, 2H, H-2′), 3.29-3.33 and 3.43-3.46 (2×m, 2H, H-5′), 3.81 (s, 6H, 2×OMe), 4.05-4.08 (m, 1H, H-3′), 4.41-4.45 (m, 1H, H-4′), 6.30-6.34 (t, J=6.4 Hz, 1H, H-1′), 6.86-7.56 (m, 18H, arom-H), 7.88 (s, 1H, NH), 8.32 (s, 1H, H-6). 13C NMR (100 MHz, DMSO) δ: −4.89 and −4.69 [Si(CH3)2], 1.03 (SeCH3), 17.95 [SiC(CH3)], 25.73 [SiC(CH3)], 41.86 (C-2′), 55.26 (OMe), 63.05 (C-5′), 72.41 (C-3′), 86.30 (C-4′), 86.77 (C-5), 87.24 (C-1′), 113.27 (arom-C), 127.07 (arom-C), 128.13 (arom-C), 128.27 (arom-C), 129.38 (arom-C), 130.09 (arom-C), 132.67 (arom-C), 133.68 (C-6), 135.51 (NHCO), 144.41 (arom-C), 144.36 (C-2), 158.69 (C-4). HR-MS (ESI-TOF, negative ion mode): molecular formula, C44H51N3O7SeSi: [M−H]−: 840.2570 (calc. 840.2583)

Aufarbeitung

  1. dry with materialdried on high vacuum for one hour before addition of anhydrous pyridine 10 ml
  2. extractionthe crude product was extracted with saturated NaCl solution and ethyl acetate
  3. customThe organic phase was removed
  4. extractionaqueous phase was extracted with ethyl acetate three times
  5. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  6. filtrationthe salt was filtered
  7. customthe organic solvents were evaporated under reduced pressure
  8. customThe residue was purified on a silica gel column (equilibrated with hexane)
  9. washeluted with an ethyl acetate/hexane gradient (EtOAc in hexane, 10-50%)

Quellen und Nachweise

ORD-Eintrag
ord-f9479dca18584e6f83a6cdc752a979ac
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08809357B2

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