✦ LIBER ✦
Deoxy-nitrosugars. 9th communication. Chain elongation of 1-C -nitroglycosyl halides by substitution with some weakly basic carbanions
✍ Scribed by Bernrd Aebischer; Roger Meuwly; Andrea Vesella
- Publisher
- John Wiley and Sons
- Year
- 1984
- Tongue
- German
- Weight
- 397 KB
- Volume
- 67
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
The 1‐C‐nitroglycosyl chloride reacted with the anions form 2‐nitropropane, nitromethane, and diethyl malonate, to give the chain‐extended products 2 (81%), 5 (72%), and 6 (83%), respectively. Treatment of the 1‐C ‐nitroglycosyl bromide 7 by the lithium salt obtained form 8 gave the dodecodiulose derivative 9 (76%). Th β‐D‐configuration of 2 and 9 was inferred form their NMR and CD spectra. Treatment of 2 and 9 with sodium sulfide gave the enol ethers 3 (96%) and 10 (92%), respectively. The (Z)‐configuration of 10 was deduced form the configuration of its hydrogenation product 11.