Triacetate of 7-oxabicyclo[2.2.1]hept-5-ene-1,2-exo,3-exo-trimethanol was converted selectively into (1RS,2SR,5RS,6RS)-4,5,6-tris(acetoxymethyl)-2-bromocyclohex-3-en-1-ol (4) or into (1RS,2SR,5RS,6RS)-5,6-bis(acetoxymethyl)-2-bromo-4-bromomethylcyclohex-3 -en-1-ol (12). These products were displaced with azide anion and transformed into (1RS,2RS,5RS,6RS)-2-amino-4,5,6-tris(hydroxymethyl)cyclohex-3-en-1-ol (7) and (1RS,2RS,5RS,6RS)-2-amino-4-aminomethyl-5,6-bis(hydroxymethyl)cyclohex-3 -en-1-ol (15), respectively. (1RS,2SR,3RS,4SR,5RS,6SR)-3-Amino-1,5,6-tris(hydroxymethyl)cyclohexa-1,2 ,4-triol (11) was also derived from 4.
Type
research article
Authors
Publication date
1998
Published in
Issue
11
Start page
1237
End page
1239
Note
Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland.
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
November 9, 2005
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