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

HRID 1625727노트

반응식

HRID 1625727 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6343Ethanethiol용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4e8a368ac9a04118b9bf2a9ad561257e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785403B2

반응 노트

불러오는 중…