2-Naphthalenethiol → 2-naphthalenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 5998

Reaktionsgleichung

Reaktionsgleichung von HRID 5998
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[SH:11].[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:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:19])[CH3:18]

Komponenten

4

Edukt 3

HCID 70582-NaphthalenethiolHCID 11591Mercuric cyanideHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Produkt 1

HCID 147953672-naphthalenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideAusbeute 40 %

Versuchsvorschrift

If the procedure described in Preparation I is followed starting from 6.8 g (42.4.10-3 mol) of naphthalene-2-thiol, 10.8 g (42.4.10-3 mol) of mercuric cyanide, Hg(CN)2, and 12 g (33.2.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 5.84 g (yield: 40%) of the expected product are obtained.

Aufarbeitung

  1. customIf the procedure described in Preparation I

Quellen und Nachweise

ORD-Eintrag
ord-69dfd454486f4733968831d54991e21b
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246961

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