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

HRID 74854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74854
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-adf419bf9c364feaab2d6a472809da37
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828952B2

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