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

HRID 2372975

Reaktionsgleichung

Reaktionsgleichung von HRID 2372975
[N+:1]([C:4]1[CH:5]=[C:6]([SH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Hg](C#N)C#N.[C:16]([O:19][C@@H:20]1[C@@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:24]([O:30][C:31](=[O:33])[CH3:32])[CH2:23][S:22][C@@H:21]1Br)(=[O:18])[CH3:17]>>[C:16]([O:19][C@@H:20]1[C@@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:24]([O:30][C:31](=[O:33])[CH3:32])[CH2:23][S:22][C@H:21]1[S:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:18])[CH3:17]

Komponenten

4

Edukt 3

HCID 11591Mercuric cyanideHCID 2435763-Nitrobenzene-1-thiolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Produkt 1

HCID 147953553-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideAusbeute 27 %

Versuchsvorschrift

If the procedure described in Preparation I is followed starting from 10 g (64.5.10-3 mol) of 3-nitrobenzenethiol, 16.29 g (64.5.10-3 mol) of mercuric cyanide (Hg(CN)2) and 25.2 g (70.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 7.44 g (yield: 27%) of the expected product are obtained after purification by flash chromatography using a toluene/ethyl acetate mixture (9/1 v/v) as the eluent, followed by crystallization from ether.

Aufarbeitung

  1. customIf the procedure described in Preparation I

Quellen und Nachweise

ORD-Eintrag
ord-e7bb70f2eddc4cc28b9b94fc9bec30b9
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05101048

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