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- Title
A Stereoselective Synthesis of an Imino Glycal: Application in the Synthesis of (–)‐1‐epi‐Adenophorine and a Homoimindosugar.
- Authors
Chennaiah, Ande; Dahiya, Amit; Dubbu, Sateesh; Vankar, Yashwant D.
- Abstract
A concise stereoselective synthesis of an imino glycal is described in 8 steps starting from 1,2‐anhydro‐3,4,6‐tri‐O‐benzyl‐d‐glucopyranose. The utility of the imino glycal has been demonstrated in synthesis of (–)‐1‐epi‐adenophorine and a homoiminosugar as a glycosidase inhibitor. The important features of the developed route include high yields, high stereoselectivity, and application in the synthesis of other iminosugars. Additionally, a new synthon 2‐nitro‐imino glycal has also been synthesized which could act as valuable synthon in carbohydrate chemistry. A simple and efficient stereoselective synthesis of an imino glycal is demonstrated in 8 steps starting from 1,2‐anhydro‐3,4,6‐tri‐O‐benzyl‐d‐glucopyranose. The utility of the imino glycal has been shown in synthesis of (–)‐1‐epi‐adenophorine and a homoiminosugar as a glycosidase inhibitor.
- Subjects
STEREOSELECTIVE reactions; GLYCALS; ORGANIC synthesis; GLYCOSIDASE inhibitors; CARBOHYDRATES
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 46, p6574
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201801241