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

HRID 1625727Notes

Reaction equation

HRID 1625727 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6343EthanethiolSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-4e8a368ac9a04118b9bf2a9ad561257e
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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