Interconversion of the ends of D-ribese 2 afforded in 6 steps and 45% overall yield L-ribose 1, from which 2-deoxy L-ribose 12 was easily prepared. In addition, the inexpensive L-arabinose 13 was also converted into 2-deoxy L-ribose 12 via a reductive radical rearrangement of the arabinopyranosyl br
The total syntheses of 2-deoxy-DL- and L-riboses
โ Scribed by Gen Nakaminami; Masazumi Nakagawa; Sachiko Shioi; Yoko Sugiyama; Satoko Isemura; Mikio Shibuya
- Publisher
- Elsevier Science
- Year
- 1967
- Tongue
- French
- Weight
- 210 KB
- Volume
- 8
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
We report herein the total synthe.ses of 2-deoxy-DL-and L-rlboses. As Illustrated in the following scheme, the Reformatsky reaction of ethyl bromoaoetate with aoroleln afforded the p-hydroxy eater (I) in a yield of 40-502, whloh was hydrolysed by means of aqueous potassium hydroxide to give the DL-acid (II, 85s yield). The hydroxy acid (II) in an aqueous solution was treated with
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