✦ LIBER ✦
Stereoelectronic effects in the ring cleavage of methyl glycopyranosides using dimethylboron bromide
✍ Scribed by Yvan Guindon; Paul C. Anderson
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 273 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
SUmTkiry: Treatment of methyl D-glycopyranosides with dimethylboron bromide followed by a nucleophile gives acyclic products resulting from selective cleavage of the ring carbon-oxygen bond. The results are rationalized based on stereoelectronic considerations. We previously describedC the reaction of dimethylboron bromide (Me2BBr) with methyl glycosides at room temperature, to give in good yield, glycosyl bromides, useful intermediates in the synthesis of Q-. S-and C-glycosides. Recently3 we have shown that the endocyclic