A convenient synthesis of 4-thio-D-galactofuranose
β Scribed by Varela, Oscar; Cicero, Daniel; De Lederkremer, Rosa M.
- Book ID
- 120348509
- Publisher
- American Chemical Society
- Year
- 1989
- Tongue
- English
- Weight
- 990 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
ABSTRACr 5-0-Methyl-D-galactofuranose (7) was synthesized, for the first time, in five steps from D-galactono-1,4-lactone (1) in good overall yield. Tritylation and further acetylation of 1 gave 2,3,5-tri-O-acetyl-6-O-trityl-D-galactono-l,Clactone (2); prolonged acetylation caused elimination to for
Benzoylation of o-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23", gave the 2,6-dibenzoate (2,62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-0-benzoyl-a#o-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-0-(2,3,5,6-tetra-O-~nzoyl-~-o-galactofuranosyl)-~galact