Boron trifluoride etherate → HCID 86600676, compound

HRID 1443759Notes

Reaction equation

HRID 1443759 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C:10]1([C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[C:43]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][Si](C(C)(C)C)(C)C)=[CH:51][CH:50]=2)[CH:42]=1)[OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](C(C)C)C(C)C)(C)C.B(F)(F)F.CCOCC.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:11][C@@:10]1([C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[C:43]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=2)[CH:42]=1)[OH:40])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherate2×HCID 11430Potassium CarbonateHCID 138754Silane, tris(1-methylethyl)-2×HCID 44600131HCID 44600131, compound

Product 1

HCID 86600676HCID 86600676, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 0.48 g (approx. 88% pure) 1-(2,3,4,6-tetra-O-benzyl-1-hydroxy-D-glucopyranosyl)-3-[4-(tert-butyl-dimethyl-silyloxy)-benzyl]-4-methyl-benzene in 3.5 mL dry acetonitrile is cooled to −40° C. under argon. 0.13 mL triisopropylsilane and 0.08 mL boron trifluoride etherate are added dropwise. The solution is stirred for 3 h at −35° C., before another 0.02 mL of triisopropylsilane and 0.01 mL of boron trifluoride etherate are added. After a further 2 h at −40° C. aqueous potassium carbonate solution is added, and the resulting mixture is stirred for 1 h at ambient temperature. Then water is added and the mixture is extracted four times with ethyl acetate. The organic phase is dried over sodium sulfate, concentrated and chromatographed on silica gel (cyclohexane/ethyl acetate 10:1->4:1).

Workup

  1. additionare added
  2. extractionthe mixture is extracted four times with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. customchromatographed on silica gel (cyclohexane/ethyl acetate 10:1->4:1)

Sources & evidence

ORD record
ord-275dc0da507f494686a3344d40868692
Source dataset
uspto-grants-2010_02
Patent number
US07662790B2

Reaction notes

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