Thymine → HCID 22844870、化合物

HRID 653982

反応式

HRID 653982 の反応式
C(O[CH:5]1[S:9][C@H:8]([CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:6]1)(=O)C.[NH:29]1[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]1=[O:31].FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S([O-])(=O)=O.[K+].C[Si](N[Si](C)(C)C)(C)C.[Si](Cl)(C)(C)C>>[Si:12]([O:11][CH2:10][C@H:8]1[S:9][C@@H:5]([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[CH2:6][CH2:7]1)([C:25]([CH3:26])([CH3:27])[CH3:28])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 5

HCID 1135ThymineHCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 151260981-O-Acetyl-5-O-t-butyldiphenylsilyl-4-thio-2,3-dideoxyribofuranoseHCID 23675274Potassium perfluorobutanesulfonate

生成物 1

HCID 22844870HCID 22844870、化合物収率 93%

実験手順

Using the procedure for Example 11, 4'-thioribose 10 (0.35 g, 0.83 mmol), thymine (0.13 g, 1.05 mmol), potassium nonafluorobutanesulfonate (0.875 g, 2.54 mmol), HMDS (0.175 mL, 0.83 mmol), and TMS-Cl (0.4 mL, 3.2 mmol), following purification by preparative TLC (8:1 dichloromethane/acetonitrile) afforded 371 mg (92.5%) of 14, as a 4:3 α:β anomeric mixture; FAB MS 481 (M+H)+ ; 1H NMR (CDCl3) δ 9.65 (s, 1, NH), 7.7 (m, 4, ArH), 7.4 (m, 6, ArH), 6.3 (m, 1, 1'-Hα,β), 3.88 (m, 1, 4'-Hα), 3.82 (d, 1, 5'-Hβ), 3.66 (d+m, 2, 4'-Hβ, 5'-Hα), 2.4-1.85 (m, 4, 2'-H α,β 's, 3'-Hα,β 's), 1.95 (s, 3, 5β -CH3), 1.77 (s, 3, 5β -CH3), 1.11 (s, 9, β-t-butyl), 1.07 (s, 9, α-t-butyl).

後処理

  1. custompurification by preparative TLC (8:1 dichloromethane/acetonitrile)

出典と根拠

ORDレコード
ord-facf6c4543be4f8b90dcebbd7b50b351
出典データセット
uspto-grants-1992_07
特許番号
US05128458

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