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

HRID 74854ノート

反応式

HRID 74854 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-adf419bf9c364feaab2d6a472809da37
出典データセット
uspto-grants-2014_09
特許番号
US08828952B2

反応ノート

読み込み中…