Mercuric cyanide → 2,4-dicyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 6020

Reaktionsgleichung

Reaktionsgleichung von HRID 6020
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[SH:11])[C:6]#[N:7])#[N:2].[Hg](C#N)C#N.[C:17]([O:20][C@@H:21]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:25]([O:31][C:32](=[O:34])[CH3:33])[CH2:24][S:23][C@@H:22]1Br)(=[O:19])[CH3:18]>>[C:17]([O:20][C@@H:21]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:25]([O:31][C:32](=[O:34])[CH3:33])[CH2:24][S:23][C@H:22]1[S:11][C:10]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:1]#[N:2])(=[O:19])[CH3:18]

Komponenten

4

Edukt 3

HCID 11591Mercuric cyanide2×HCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromideHCID 147953364-Sulfanylbenzene-1,3-dicarbonitrile

Produkt 1

HCID 147953632,4-dicyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideAusbeute 40,5 %

Versuchsvorschrift

If the procedure described in Preparation I is followed starting from 1.5 g (9.10-3 mol) of 3-cyano-4-mercaptobenzonitrile, 2.78 g (11.10-3 mol) of mercuric cyanide, Hg(CN)2, and 3.66 g (11.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1.65 g (yield: 40.5%) of the expected product are obtained.

Aufarbeitung

  1. customIf the procedure described in Preparation I

Quellen und Nachweise

ORD-Eintrag
ord-b55aa83528f442f49b35d1e8c285a53a
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246961

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