A concise synthesis of α-glycosyl cyanides
✍ Scribed by Yasuhiro Igarashi; Tatsushi Shiozawa; Yoshitaka Ichikawa
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- English
- Weight
- 257 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0960-894X
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✦ Synopsis
A simple procedure has been developed for the synthesis of c~-glycosyl cyanides: reactions of O-benzylated ethyl 1-thio-glycosides of L-fucose and D-glucose, with TMSCN and MeOTf in ether exclusively gave the corresponding ec-glycosyl cyanides in good yields.
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The treatment of glycals with allyltrimethylsilane, trimethylsilyl cyanide and trimethylsilyl azide in the presence of catalytic amounts of Sc(OTf) 3 gave the corresponding 2,3-unsaturated allyl glycosides, glycosyl cyanides and glycosyl azides in excellent yields with high a-selectivity.
Asymmetric synthesis of various glycosyl-ct-aminoacids is described. The approach involves the diastereoselective condensation of glycine enolates on the carbonyl in position 3 of the suitably protected et-D-ribohexofuranos-3-ulose.