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Synthesis of α-C-glycosides via tandem Tebbe methylenation and Claisen rearrangement

✍ Scribed by H.Yasmin Godage; Antony J. Fairbanks

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
264 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A variety of a-C-glycosides may be accessed in an entirely stereoselective fashion from 3-OH glycal esters, by way of the tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. In contrast with previous studies in the corresponding b-series, careful control of conditions for Claisen rearrangement is required in order to avoid loss of integrity of anomeric stereochemistry; thermal rearrangements are best carried out in xylene in a sealed tube.

📜 SIMILAR VOLUMES

Stereoselective synthesis of C-glycoside
Stereoselective synthesis of C-glycosides via Tebbe methylenation and Claisen rearrangement
✍ H.Yasmin Godage; Antony J Fairbanks 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 141 KB

A variety of b-C-glycosides may be readily accessed in a stereoselective fashion from 3-OH glycal esters, via the use of Tebbe methylenation and subsequent thermal Claisen rearrangement. The use of carbohydrate ester substrates allows the formation of b( 16) linked C-disaccharides.

ChemInform Abstract: Synthesis of Medium
ChemInform Abstract: Synthesis of Medium-Ring Lactones via Tandem Methylenation/Claisen Rearrangement of Cyclic Carbonates.
✍ James E. P. Davidson; Edward A. Anderson; Wilm Buhr; Justin R. Harrison; Paul T. 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB 👁 2 views

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