Triethylamine → HCID 12245491、化合物

HRID 1010503ノート

反応式

HRID 1010503 の反応式
[O:1]([CH3:13])[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].CO[CH:16](OC)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)(=O)C.C(N(CC)CC)C>C(#N)C.CCCCCC.[NH4+].[NH4+].[O-][Mo]([O-])(=O)=O.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[CH3:13][O:1][C@@H:2]1[O:10][C@@H:9]2[CH2:11][O:12][CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:8][C@H:7]2[C@H:5]([OH:6])[C@H:3]1[OH:4]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 62375Benzaldehyde dimethyl acetalHCID 445238Methyl beta-D-glucopyranoside

生成物 1

HCID 12245491HCID 12245491、化合物収率 91.4%

試薬・触媒・溶媒 4

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-触媒HCID 61578Diammonium molybdate触媒HCID 6342Acetonitrile溶媒HCID 8058Hexane溶媒

実験手順

Using a modification of the procedure as described: Tetrahedron, 1992, 48(47), 10249-10264. Methyl β-D-glucopyranoside (Biosynth International M-3592; 10.2 g, 50 mmol), benzaldehyde dimethylacetal (30 ml, 200 mmol) and 10-camphorsulfonic acid (116 mg, 0.5 mmol) in anhydrous acetonitrile (150 ml) was stirred at room temperature for 4 h. The reaction was checked by TLC to confirm complete conversion to the product (run in hexane: ethyl acetate, 1:2, visualised with ceric ammonium molybdate spray and heating. The reaction was then treated with triethylamine (1 ml) to neutralise the acid. The solution was filtered and the solid was washed with acetonitrile (20 ml). The mother solution was concentrated to about 60 ml, and it was again filtrated, and the filtrate washed with acetonitdrile (10 ml). The combined solid was dried in vacuum, to give 12.9 g (91%) of methyl 4,6-O-benzylidene-β-D-glucopyranoside.

後処理

  1. temperatureheating
  2. filtrationThe solution was filtered
  3. washthe solid was washed with acetonitrile (20 ml)
  4. concentrationThe mother solution was concentrated to about 60 ml, and it
  5. filtrationwas again filtrated
  6. washthe filtrate washed with acetonitdrile (10 ml)
  7. customThe combined solid was dried in vacuum

出典と根拠

ORDレコード
ord-a901cc318ff140d2bb71347f663afade
出典データセット
uspto-grants-2011_07
特許番号
US07976824B2

反応ノート

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