Acetic Acid → 2,3,4,6-tetra-O-acetyl-5-thio-glucopyranose

HRID 2116511노트

반응식

HRID 2116511 반응식
C([O:4][CH:5]1[S:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C(O)(=O)C.Cl>CN(C)C=O.CNN>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[S:22][CH:5]1[OH:4])(=[O:10])[CH3:9]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 11654362(3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-thiopyran-2,3,4,5-tetrayl tetraacetate

생성물 1

HCID 116462702,3,4,6-tetra-O-acetyl-5-thio-glucopyranose수율 88.2%

시약·촉매·용매 2

HCID 6061Methylhydrazine촉매HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 1,2,3,4,6-penta-O-acetyl-5-thio-D-glucopyranose (34.0 g, 0.0837 mol) in N,N-dimethylformamide (200 mL), a mixture of methylhydrazine (6.70 mL, 0.125 mmol), acetic acid (7.2 mL, 0.125 mol) and N,N-dimethylformamide (25 mL) was added under ice cooling. After stirring the raction mixture at room temperature for 2.5 hours, 0.5M HCl (300 mL) was added under ice cooling, and the resulting mixture was then extracted twice with ethyl acetate (250 mL). The combined organic phases were washed sequentially with water (200 mL), saturated aqueous NaHCO3 (100 mL), water (100 mL) and saturated aqueous sodium chloride (100 mL), followed by addition of MgSO4 and activated charcoal (1 g). After filtration to remove the insoluble materials, the filtrate was concentrated under reduced pressure. The resulting residue was crystallized from isopropyl ether (70 mL) to give 2,3,4,6-tetra-O-acetyl-5-thio-glucopyranose (26.9 g, 88%) as a colorless crystal.

후처리

  1. additionwas added under ice cooling
  2. extractionthe resulting mixture was then extracted twice with ethyl acetate (250 mL)
  3. washThe combined organic phases were washed sequentially with water (200 mL), saturated aqueous NaHCO3 (100 mL), water (100 mL) and saturated aqueous sodium chloride (100 mL)
  4. additionfollowed by addition of MgSO4 and activated charcoal (1 g)
  5. filtrationAfter filtration
  6. customto remove the insoluble materials
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was crystallized from isopropyl ether (70 mL)

출처 및 근거

ORD 기록
ord-49d9740b8dff49dc83ed048e09422793
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07439232B2

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