Boron trifluoride etherate → (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-[4-[2-(tritylamino)ethyl]benzyl]phenyl]-D-glucitol

HRID 1009867Notes

Reaction equation

HRID 1009867 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:12][C:10]1([C:41]1[CH:46]=[C:45]([CH:47](O)[C:48]2[CH:53]=[CH:52][C:51]([CH2:54][CH2:55][NH:56][C:57]([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)([C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[CH:50][CH:49]=2)[C:44]([CH3:77])=[CH:43][C:42]=1[O:78][CH2:79][C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C(#N)C>[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:12][C@H:10]1[C:41]1[CH:46]=[C:45]([CH2:47][C:48]2[CH:49]=[CH:50][C:51]([CH2:54][CH2:55][NH:56][C:57]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)([C:70]3[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=3)[C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)=[CH:52][CH:53]=2)[C:44]([CH3:77])=[CH:43][C:42]=1[O:78][CH2:79][C:80]1[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 866384412,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-[hydroxy[4-[2-(tritylamino)ethyl]phenyl]methyl]-4-methylphenyl]-D-glucopyranose

Product 1

HCID 86638440(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-[4-[2-(tritylamino)ethyl]benzyl]phenyl]-D-glucitolYield 64.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile solution (6 mL) of 2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-[hydroxy[4-[2-(tritylamino)ethyl]phenyl]methyl]-4-methylphenyl]-D-glucopyranose (0.638 g, 0.565 mmol) were added under nitrogen atmosphere at 0° C. Et3SiH (0.27 mL, 1.695 mmol) and BF3.Et2O (1.58 mL, 1.24 mmol), and the mixture was stirred for 30 minutes at the same temperature. To the reaction solution cooled in ice was added a saturated sodium bicarbonate aqueous solution and the resulting mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain the title compound (0.402 g, 59%) as a pale yellow oily compound.

Workup

  1. temperatureTo the reaction solution cooled in ice
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe solvent was evaporated under reduced pressure
  6. customThus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-9aeb0392e0f149e5b3910bdd57652595
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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