SYNTHESIS OF DEOXY DERIVATIVES OF THE GLUCOSINOLATES GLUCOTROPAEOLIN AND GLUCOBRASSICIN

Authors
STREICHER H LATXAGUE L WIEMANN T ROLLIN P THIEM J
Citation
H. Streicher et al., SYNTHESIS OF DEOXY DERIVATIVES OF THE GLUCOSINOLATES GLUCOTROPAEOLIN AND GLUCOBRASSICIN, Carbohydrate research, 278(2), 1995, pp. 257-270
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Carbohydrate research → ACNP
ISSN journal
00086215
Volume
278
Issue
2
Year of publication
1995
Pages
257 - 270
Database
ISI
SICI code
0008-6215(1995)278:2<257:SODDOT>2.0.ZU;2-0
Abstract
The syntheses of ri-O-acetyl-2-deoxy-1-thio-D-arabino-hexopyranose, 2, 4,6-tri-O-acetyl 3-deoxy-1-thio-beta-D-ribo-hexopyranose, O-benzoyl-4- deoxy-1-thio-beta-o-xylo-hexopyranose, and 4-tri-O-acetyl-6-deoxy-1-th io-beta-D-glucopyranose are reported. These thiols were coupled with p henylacetohydroximoyl chloride or indol-3-ylacetohydroximoyl chloride, respectively. Sulfation and subsequent deprotection yielded the corre sponding deoxy derivatives of glucotropaeolin and glucobrassicin, two major representatives of the glucosinolate family.