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

HRID 74854노트

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HRID 74854 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-adf419bf9c364feaab2d6a472809da37
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828952B2

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