Reaktion #6094

ord-69dfd454486f4733968831d54991e21b

Reaktionsgleichung

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide
Sc1ccc2ccccc2c1
naphthalene-2-thiol
N#[C][Hg][C]#N
Hg(CN)2
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc3ccccc3c2)SC[C@H]1OC(C)=O
expected product
Ausbeute 40.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc3ccccc3c2)SC[C@H]1OC(C)=O
2-naphthalenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Ausbeute 40.0%

Edukte

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide
Sc1ccc2ccccc2c1
naphthalene-2-thiol
—
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeIf the procedure described in Preparation I

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246961uspto-grants-1993_09