Boron trifluoride etherate → HCID 131716687, compound

HRID 1073461Notes

Reaction equation

HRID 1073461 reaction equation
[F:1][C:2]([F:39])([C:8]1([O:29][C@H:28]([CH2:30][O:31][CH2:32][C:33]2C=CC=CC=2)[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:10]1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].B(F)(F)F.[CH3:44][CH2:45][O:46]CC.C(=O)(O)[O-:50].[Na+]>C(OC(=O)C)(=O)C.CCOCC>[C:45]([O:9][C:8]1([O:29][C@H:28]([CH2:30][O:31][C:32](=[O:50])[CH3:33])[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:10]1[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:2]([F:39])([F:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:46])[CH3:44]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 131716688HCID 131716688, compound

Product 1

HCID 131716687HCID 131716687, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a stirred solution of 2.40 g of 2-deoxy-2,2-difluoro-4,5,7-tris-O-(phenylmethyl)-D-arabino-3-heptulofuranosonic acid, ethyl ester in 8.8 ml of acetic anhydride at 0° C. was added 1.08 ml of boron trifluoride etherate. After 2 hours at 0° C., the solution was diluted with ether and stirred with aqueous sodium bicarbonate solution. The organic layer was washed with water and brine, dried, and concentrated. The residue was subjected to column chromatography on silica gel to give an oil, CMR δ 20.7 and 215 (singlets, CH3CO).

Workup

  1. washThe organic layer was washed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. customto give an oil, CMR δ 20.7 and 215 (singlets, CH3CO)

Sources & evidence

ORD record
ord-24c8ac81497e4b04b207bb70ae1cd9a2
Source dataset
uspto-grants-1990_11
Patent number
US04968790

Reaction notes

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