4-Toluenesulfonyl chloride → (3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol

HRID 327774

Reaktionsgleichung

Reaktionsgleichung von HRID 327774
[O:1]=[C:2]1[CH2:27][C@@H:26]2[C@:13]([CH3:30])([CH2:14][CH2:15][C@H:16]3[C@H:25]2[CH2:24][CH:23]=[C:22]2[C@:17]3([CH3:29])[CH2:18][CH2:19][C@H:20]([OH:28])[CH2:21]2)[C@H:3]1[C@H:4]([CH3:12])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:11])[CH2:9][OH:10].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O>[OH:1][C@H:2]1[CH2:27][C@@H:26]2[C@:13]([CH3:30])([CH2:14][CH2:15][C@H:16]3[C@H:25]2[CH2:24][CH:23]=[C:22]2[C@:17]3([CH3:29])[CH2:18][CH2:19][C@H:20]([OH:28])[CH2:21]2)[C@H:3]1[C@H:4]([CH3:12])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:11])[CH2:9][OH:10]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 13873472(25R)-16-oxo-26-hydroxycholesterol

Produkt 1

HCID 11729441(3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diolAusbeute 160,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (25R)-26-hydroxy-16-oxocholesterol (9) (4.52 mmoles in pyridine (20 ml)), cooled in an ice bath, p-toluenesulfonyl chloride (3.44 g, 18.0 mmoles) is added mixture is stirred for 5 hours at room temperature. The reaction mixture is then poured into water and extracted with ether. The organic layer is washed with 2N HCl and water, dried over sodium sulfate, and evaporated under reduced pressure to yield 3.04 g (93%) of (25R)-16β, 26-dihydroxycholesterol 3β, 26-ditosylate (7) as an oil. The product is the same as the one in Example 8.

Aufarbeitung

  1. extractionextracted with ether
  2. washThe organic layer is washed with 2N HCl and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cee6e31dcfc14cb0a03a3e1ffc9785b2
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05274088

Verknüpfte Notizen

Wird geladen…