Boron trifluoride → 1-(beta-D-glucopyranosyl)-4-chloro-3-(5-(2-pyrimidinyl)-2thienylmethyl)benzene

HRID 1625727ノート

反応式

HRID 1625727 の反応式
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@H:10]1[C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[C:42]([CH2:47][C:48]2[S:49][C:50]([C:53]3[N:58]=[CH:57][CH:56]=[CH:55][N:54]=3)=[CH:51][CH:52]=2)[CH:41]=1)C1C=CC=CC=1.B(F)(F)F.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(S)C>[C@@H:10]1([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[C:42]([CH2:47][C:48]3[S:49][C:50]([C:53]4[N:54]=[CH:55][CH:56]=[CH:57][N:58]=4)=[CH:51][CH:52]=3)[CH:41]=2)[O:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]1[OH:8]

参加物

6

反応物 4

HCID 6356Boron trifluorideHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 115423881-(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)-4-chloro-3-(5-(2-pyrimidinyl)-2-thienylmethyl)benzene

生成物 1

HCID 114422751-(beta-D-glucopyranosyl)-4-chloro-3-(5-(2-pyrimidinyl)-2thienylmethyl)benzene収率 54.1%

試薬・触媒・溶媒 1

HCID 6343Ethanethiol溶媒

反応条件

温度
0 °C

実験手順

To a solution of the above 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4-chloro-3-(5(2-pyrimidinyl)-2-thienylmethyl)benzene 55 (90 mg) in ethanethiol (1.5 ml) was added boron trifluoride.ether complex (0.42 ml) at 0° C., and the mixture was stirred at room temperature overnight. The mixture was cooled again to 0° C., and added thereto were a saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium thiosulfate solution. The mixture was extracted with ethyl acetate and tetrahydrofuran, and the extract was dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=19:1-9:1) to give the desired 1-(β-D-glucopyranosyl)-4-chloro-3-(5-(2-pyrimidinyl)-2-thienylmethyl)benzene 56 (27 mg) as pale yellow powder. APCI-Mass m/Z 449/451 (M+H).

後処理

  1. temperatureThe mixture was cooled again to 0° C.
  2. additionadded
  3. extractionThe mixture was extracted with ethyl acetate and tetrahydrofuran
  4. dry with materialthe extract was dried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=19:1-9:1)

出典と根拠

ORDレコード
ord-4e8a368ac9a04118b9bf2a9ad561257e
出典データセット
uspto-grants-2014_07
特許番号
US08785403B2

反応ノート

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