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3,4-dihydro-2H-pyran → tetrahydro-2H-pyran-2-yl 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose

HRID 604703
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 604703
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[C:7]([O:10][C@@H:11]1[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([O:22][C:23](=[O:25])[CH3:24])[C@@H:15]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[S:14][CH:12]1[OH:13])(=[O:9])[CH3:8].C(=O)(O)[O-].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)(Cl)Cl>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:12]1([S:14][C@H:15]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C@@H:16]([O:22][C:23](=[O:25])[CH3:24])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:11]1[O:10][C:7](=[O:9])[CH3:8])[OH:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 116462702,3,4,6-tetra-O-acetyl-5-thio-glucopyranose

Produkt 1

HCID 131728755tetrahydro-2H-pyran-2-yl 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranoseAusbeute 104 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998
p-Toluenesulfonic acid monohydrate
Katalysator
HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

3,4-Dihydro-2H-pyran (1.5 mL, 16.5 mmol) and p-toluenesulfonic acid monohydrate (104 mg, 0.549 mmol) were added to a chloroform (40 mL) solution of 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose (2.0 g, 5.49 mmol) and stirred at room temperature for one hour. The reaction mixture was added with a saturated sodium bicarbonate aqueous solution and extracted with chloroform, and after the organic layer was washed with brine, it was dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain pale yellow amorphous tetrahydro-2H-pyran-2-yl 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose (2.56 g).

Aufarbeitung

  1. extractionextracted with chloroform
  2. washafter the organic layer was washed with brine, it
  3. dry with materialwas dried with anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained
  6. customby evaporating the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-966c3aa90b5e4904bf3e31643ec04b5a
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07910619B2

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