Boron trifluoride etherate → Allyl 2,3,4-tri-O-benzyl-A-D-glucopyranoside

HRID 53838Notes

Reaction equation

HRID 53838 reaction equation
B(F)(F)F.CCOCC.[CH2:10]([O:17][C@@H:18]1[C@@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:26]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:25]([CH2:44][O:45]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:24][C@@H:19]1[O:20][CH2:21][CH:22]=[CH2:23])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[SiH](CC)(CC)CC.C([O-])(O)=O.[Na+]>CC#N.C(Cl)Cl.O>[CH2:10]([O:17][C@@H:18]1[C@@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:26]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:25]([CH2:44][OH:45])[O:24][C@@H:19]1[O:20][CH2:21][CH:22]=[CH2:23])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 21591620Allyl 2,3,4-tri-O-benzyl-6-O-trityl-alpha-D-glucopyranoside

Product 1

HCID 12041116Allyl 2,3,4-tri-O-benzyl-A-D-glucopyranoside

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of BF3.OEt2 (5.0 ml, 39.8 mmol) in MeCN (90 ml) was added dropwise to a cooled (0°) solution of 3 (13.4 g, 18.3 mmol) and Et3SiH (14.5 ml, 91.5 mmol) in dry CH2Cl2 (150 ml). After 10 min., a sat. aq. solution of NaHCO3 (100 ml) and H2O (200 ml) were added. The mixture was shaken vigorously, the aq. layer was extracted with CH2Cl2, the combined organic layers were extracted with brine, dried (MgSO4), and evaporated. FC (400 g SiO2, EtOAc/hexane 1:5→EtOAc/hexane 1:1) affored 8.35 g (93%) of 4. Rf (EtOAc/hexane 1:2) 0.20.

Workup

  1. extractionthe aq. layer was extracted with CH2Cl2
  2. extractionthe combined organic layers were extracted with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-85ac7f0dd942407aa574ca1e80abd70e
Source dataset
uspto-grants-1997_04
Patent number
US05621002

Reaction notes

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