Formation and Reactions of Glycal Derivatives
β Scribed by Waldemar Priebe; Grzegorz Grynkiewicz
- Book ID
- 101936747
- Publisher
- John Wiley and Sons
- Year
- 2003
- Weight
- 52 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0931-7597
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π SIMILAR VOLUMES
5-O-alpha-D-Glucopyranosyl-beta-D-fructopyranose (leucrose, 1) was transformed into 3,4-di-O-acetyl-1-O-methanesulfonyl-5-O-(2,3,4-tri-O-acetyl-6-O-methanes ulfonyl-alpha-D-glucopyranosyl)-beta-D-fructopyranosyl bromide (3) and 1,3,4-tri-O-benzoyl-5-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl)
Treatment of a solution of the 2-O-(NJ+dimethylsulfamoyl) derivative 3 of the levoglucosenone-derived carbocycle 1 in liquid ammonia at -40 to -50" with sodium metal gave 73% of the glycal derivative 4 instead of the expected 2-deoxy derivative (2) of 1. Under the same conditions, the 2-O-(NJ-dimeth