4-Toluenesulfonyl chloride → 1,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol 5-(4-Methylbenzenesulfonate)

HRID 1290439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1290439
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C@@H:11]2[C@@H:15]([OH:16])[C@H:14]([CH2:17][OH:18])[O:13][CH2:12]2)=[CH:5][CH:4]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:18][CH2:17][C@@H:14]2[O:13][CH2:12][C@H:11]([S:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C@H:15]2[OH:16])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 676483351,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol

Produkt 1

HCID 883371051,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol 5-(4-Methylbenzenesulfonate)Ausbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a 0° C. solution, under argon, of 0.580 g of product from Example 323 in 10 ml of pyridine is added 0.430 g of p-toluenesulfonyl chloride. The reaction is stirred at room temperature overnight. The mixture is quenched with water, extracted with diethyl ether, washed with water and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by chromatography (Silica gel: 50% ethyl acetate/hexane) to give 0.520 g of the desired product.

Aufarbeitung

  1. customThe mixture is quenched with water
  2. extractionextracted with diethyl ether
  3. washwashed with water and saturated sodium chloride
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography (Silica gel: 50% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1c12c551d864427aacf603d06842b36e
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750735

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