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Boron trifluoride etherate → (2-Methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranoside

HRID 592115
Notes
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Reaction equation

HRID 592115 reaction equation
C(O[C@@H:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:31][C:30]=1[SH:39].B(F)(F)F.CCOCC>C(Cl)Cl>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:22][C@H:5]1[S:39][C:30]1[CH:31]=[C:32]([C:35]([CH3:37])([CH3:36])[CH3:38])[CH:33]=[CH:34][C:29]=1[CH3:28])(=[O:10])[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 5968682-Methyl-5-tert-butylthiophenolHCID 2724702beta-D-Glucose pentaacetate

Product 1

HCID 86725163(2-Methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranosideYield 85%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

1,2,3,4,6-Penta-O-acetyl-β-D-glucopyranose 8 (30 g, 77 mmol) was dissolved in anhydrous DCM (34 mL). 2-Methyl-5-tert-butyl thiophenol (17 mL, 92 mmol, 1.2 eq) were added under stirring. BF3.OEt2 (13.6 mL, 108 mmol, 1.4 eq) was added dropwise and the resulting yellow solution was stirred over night. After completion the solution was diluted with DCM and extracted with saturated aqueous NaHCO3 and H2O, and the organic layer was dried over MgSO4. The solvent was evaporated in vacuo and the residue was dried in high vacuum. The resulting yellow solid was purified by column chromatography on silica gel (cyclohexane/ethyl acetate) to afford 9 (33.4 g, 65.4 mmol, 85%). [α]D20=−8.0° (c=1.0, CHCl3); IR (CHCl3): 2961, 1747, 1366, 1211, 1034, 912 cm−1; 1H-NMR (400 MHz, CDCl3) δ 7.52 (1H, d, J 2.0, Ar—H), 7.25-7.10 (2H, m, Ar—H), 5.19 (1H, dd, J1J2 9.4, 1-H), 5.10-4.98 (2H, m, 4-H, 2-H), 4.64 (1H, d, J 10.6, 1-H), 4.23 (1H, dd, J1 12.2, J2 5.0, 6-Ha), 4.10 (1H, dd, J112.2, J2 1.9, 6-Hb), 3.71-3.63 (1H, m, 5-H), 2.34 (3H, s, CH3), 2.07-2.03 (6H, m, OAc), 2.00-1.96 (6H, m, OAc), 1.29 (9H, s, tBu); 13C-NMR (100 MHz, CDCl3) δ 170.8, 170.3, 169.5, 169.4 (C═O OAc), 149.8, 137.51, 131.47, 130.53, 130.2, 125.8, 87.0 (C-1), 75.9 (C-5), 74.2 (C-3), 70.3 (C-3), 68.3 (C-4), 62.4 (C-6), 31.4 (tBu), 20.89, 20.88, 20.74, 20.70 (OAc), 20.5 (CH3); HRMS (ESI): Calcd for C25H34O9S [M+Na]+ 533.1816. found 533.1832.

Workup

  1. stirringthe resulting yellow solution was stirred over night
  2. extractionextracted with saturated aqueous NaHCO3 and H2O
  3. dry with materialthe organic layer was dried over MgSO4
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was dried in high vacuum
  6. customThe resulting yellow solid was purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-f994f51d02ed4ee1ab07e9f992dbd90e
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238669B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes