Toluene → HCID 66969140, compound

HRID 1359927Notes

Reaction equation

HRID 1359927 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2([O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[OH:9])[CH:5]=[C:4]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([CH2:39][CH3:40])=[CH:35][CH:34]=2)[C:3]=1[CH3:41].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:50]1(B(O)O)[CH2:52][CH2:51]1.C1(C)C=CC=CC=1>O>[CH:50]1([C:2]2[CH:7]=[C:6]([C:8]3([O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]3[O:11][C:12](=[O:14])[CH3:13])[OH:9])[CH:5]=[C:4]([CH2:32][C:33]3[CH:34]=[CH:35][C:36]([CH2:39][CH3:40])=[CH:37][CH:38]=3)[C:3]=2[CH3:41])[CH2:52][CH2:51]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 66968972HCID 66968972, compound

Product 1

HCID 66969140HCID 66969140, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A flask charged with 1-bromo-3-(4-ethylbenzyl)-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene (0.30 g), potassium phosphate (0.38 g), cyclopropylboronic acid (50 mg), toluene (2 mL) and water (1 mL) is flushed with Ar for 5 min. Then, palladium acetate (11 mg) and tricyclohexylphosphonium tetrafluoroborate (36 mg) are added. The flask is tightly sealed and the mixture is stirred at 100° C. overnight. After cooling to room temperature, the mixture is diluted with water and ethyl acetate and treated with charcoal. After filtration, the organic layer is separated, washed with brine and dried (magnesium sulphate). The solvent is removed under reduced pressure and the resulting crude product is submitted to deacetylation without further purification.

Workup

  1. customis flushed with Ar for 5 min
  2. additionThen, palladium acetate (11 mg) and tricyclohexylphosphonium tetrafluoroborate (36 mg) are added
  3. customThe flask is tightly sealed
  4. temperatureAfter cooling to room temperature
  5. additionthe mixture is diluted with water and ethyl acetate
  6. additiontreated with charcoal
  7. filtrationAfter filtration
  8. customthe organic layer is separated
  9. washwashed with brine
  10. dry with materialdried (magnesium sulphate)
  11. customThe solvent is removed under reduced pressure
  12. customthe resulting crude product is submitted to deacetylation without further purification

Sources & evidence

ORD record
ord-41853f1883f94e0590b9b4b34483fb6e
Source dataset
uspto-grants-2011_02
Patent number
US07879807B2

Reaction notes

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