Conversion of D-xylose to protected D-lyxose derivatives and to D-lyxose, via the corresponding 1,2-anhydride

Citation
V. Popsavin et al., Conversion of D-xylose to protected D-lyxose derivatives and to D-lyxose, via the corresponding 1,2-anhydride, CARBOHY RES, 321(1-2), 1999, pp. 110-115
Citations number
14
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
CARBOHYDRATE RESEARCH
ISSN journal
00086215 → ACNP
Volume
321
Issue
1-2
Year of publication
1999
Pages
110 - 115
Database
ISI
SICI code
0008-6215(19990915)321:1-2<110:CODTPD>2.0.ZU;2-0
Abstract
Acid hydrolysis of 3,5-di-O-benzyl-1,2-O-cyclohexylidene-alpha-D-xylofurano se gave the corresponding lactol, which was subsequently converted to the 3 ,5-di-O-benzyl-2-O-mesyl-D-xylofuranose. This compound readily reacted with sodium methoxide, sodium benzylate or sodium hydroxide (presumably via the corresponding 1,2-anhydride) to give the protected D-lyxofuranosides. Thes e compounds were finally converted to methyl alpha-D-lyxopyranoside or to D -lyxose. (C) 1999 Elsevier Science Ltd. All rights reserved.