3-Cyanophenol → 3-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 2373008

Reaktionsgleichung

Reaktionsgleichung von HRID 2373008
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][CH:6]1Br)(=[O:3])[CH3:2].[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[C:24]#[N:25]>C1(C)C=CC=CC=1.C(#N)C.[O-2].[Zn+2]>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@H:6]1[O:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:23]([C:24]#[N:25])[CH:22]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 2

HCID 133943-CyanophenolHCID 113826832,3,4-Tri-o-acetyl-5-thioxylopyranosyl bromide

Produkt 1

HCID 150678563-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007857Zinc OxideKatalysatorHCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

If the procedure described in Preparation LXXVIII is followed starting from 0.5 g (1.4.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 0.25 g (2.1.10-3 mol) of 3-hydroxybenzonitrile and 170 mg (2.1.10-3 mol) of zinc oxide (ZnO) in 4 ml of anhydrous toluene and 4 ml of acetonitrile, 138 mg (yield: 25%) of the expected product are obtained after purification by chromatography on silica gel using a hexane/ethyl acetate mixture (2/1 v/v) as the eluent, and precipitation in ether.

Aufarbeitung

  1. customIf the procedure described in Preparation LXXVIII

Quellen und Nachweise

ORD-Eintrag
ord-b8ca2b0e148f4ed2a2bd8fe33e20eb83
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05101048

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