Sulfuric Acid → 1,2,3,4-Tetra-O-benzoyl-alpha-D-mannopyranose

HRID 74854Notes

Reaction equation

HRID 74854 reaction equation
C([O:20][CH2:21][C@H:22]1[O:36][C@H:26]([O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@H:25]([O:37][C:38](=[O:45])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@@H:24]([O:46][C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:23]1[O:55][C:56](=[O:63])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.OS(O)(=O)=O>CO>[C:28]([O:27][C@H:26]1[O:36][C@H:22]([CH2:21][OH:20])[C@@H:23]([O:55][C:56](=[O:63])[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C@H:24]([O:46][C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:25]1[O:37][C:38](=[O:45])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)(=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 674344901,2,3,4-Tetra-O-benzoyl-6-O-trityl-a-D-mannopyranose

Product 1

HCID 116357121,2,3,4-Tetra-O-benzoyl-alpha-D-mannopyranoseYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-O-Trityl-1,2,3,4-tetra-O-benzoyl-α-D-mannopyranose (5 g, 6.0 mmol), was dissolved in MeOH. H2SO4 (conc.) (150 μL) was carefully added, and the solution was stirred at room temperature overnight. The solution was poured into ice-water (300 mL) and extracted with EtOAc (80 mL). The organic layer was separated and washed with brine (80 mL), followed by NaHCO3 (sat.). The solution was dried (Na2SO4), filtered and the solvent evaporated. The crude product was purified using column chromatography (SiO2; Hex:EtOAc, 500:50 to 200:200) to yield 1.79 g of the white solid product (50%). 1H NMR (300 MHz, CDCl3) δ: 8.20-8.12 (m, 4H, Ar), 8.02-7.98 (m, 2H, Ar), 7.87-7.84 (m, 2H, Ar), 7.70-7.26 (m, 27H, Ar), 6.63 (d, 1H, J1,2=2.1, H-1), 6.12 (dd, 1H, J3,2=3.3, J3,4=10.2, H-3), 6.02 (dd, 1H, J4,3=10.0, J4,5=10.0, H-4), 5.89 (dd, 1H, J1,2=1.8, J2,3=3.1, H-2), 4.25 (ddd, 1H, H-5), 3.90-3.76 (m, 2H, H-6).

Workup

  1. extractionextracted with EtOAc (80 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (80 mL)
  4. dry with materialThe solution was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-adf419bf9c364feaab2d6a472809da37
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

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