Boron trifluoride → HCID 67116170, compound

HRID 72604Notes

Reaction equation

HRID 72604 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]2(OC)[C@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:20]2)=[CH:15][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][CH2:10][CH2:9][CH2:8]2.C([SiH](CC)CC)C.B(F)(F)F>C(#N)C.ClCCl>[Br:1][C:2]1[CH:18]=[CH:17][C:16]([CH:19]2[C@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]([O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[O:20]2)=[CH:15][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][CH2:10][CH2:9][CH2:8]2

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 67115877HCID 67115877, compound

Product 1

HCID 67116170HCID 67116170, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a stirred solution of 6-[2-bromo-5-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-2-yl)-benzyl]-chroman (900 mg, 1.05 mmol) in acetonitrile: dichloromethane (1:1 mixture, 6 mL) was added triethylsilane (0.34 mL, 2.1 mmol) and boron trifluoride diethyletharate complex (0.19 mL, 1.58 mmol), at 0° C. After stirring for 2 h, the reaction was quenched with saturated aqueous sodium bicarbonate solution. The volatiles were evaporated under reduced pressure; the resulting mixture was extracted with ethyl acetate (2×10 mL). The organic layers were combined and dried over sodium sulfate then concentrated to a residue which was purified by silica gel column chromatography to furnish 6-[2-bromo-5-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzyl]-chroman (600 mg).

Workup

  1. customat 0° C
  2. customthe reaction was quenched with saturated aqueous sodium bicarbonate solution
  3. customThe volatiles were evaporated under reduced pressure
  4. extractionthe resulting mixture was extracted with ethyl acetate (2×10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationthen concentrated to a residue which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6bdddcaa70f545a0842030c9c6a57625
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

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