Boron trifluoride etherate → HCID 86600676, compound

HRID 2245911Notes

Reaction equation

HRID 2245911 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 to the cooled solution. 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 resultant solution is stirred for 1 h at ambient temperature. Then it is diluted with water and extracted four times with ethyl acetate. The organic phase is dried over sodium sulfate, concentrated in vacuo and chromatographed through silica gel (cyclohexane/ethyl acetate 10:1→4:1).

Workup

  1. additionare added
  2. extractionextracted four times with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customchromatographed through silica gel (cyclohexane/ethyl acetate 10:1→4:1)

Sources & evidence

ORD record
ord-494341446bc940178c8a7e4b8e294201
Source dataset
uspto-grants-2010_03
Patent number
US07683160B2

Reaction notes

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