Boron trifluoride etherate → HCID 86600676, compound

HRID 2106418Notes

Reaction equation

HRID 2106418 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 is added and the 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 sulphate, concentrated 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 sulphate
  4. concentrationconcentrated
  5. customchromatographed through silica gel (cyclohexane/ethyl acetate 10:1->4:1)

Sources & evidence

ORD record
ord-c0dc5fbd0e8c4606ba40005619986804
Source dataset
uspto-grants-2009_08
Patent number
US07579449B2

Reaction notes

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