Stereoselective Synthesis of 2-(β-C-Glycosyl) glycals: Access to Unusual β-C-Glycosides from 3-Deoxyglycals

GM Reddy, BU Maheswara Rao…

Index: Gemmell, Natasha; Meo, Paul; Osborn, Helen M. I. Organic Letters, 2003 , vol. 5, # 10 p. 1649 - 1652

Full Text: HTML

Citation Number: 0

Abstract

... stability of C-glycosides(1) to acids and carbohydrate-processing enzymes has attracted many synthetic organic chemists and ... acetyl perchlorate as the Lewis acid, glucal 2 was converted to the bicyclic acetal 5 through an unprecedented 1,7-hydrogen shift(10) (Scheme 1). ...

~99%

Preparation of Anhydroalditols from Commodity Carbohydrates

[Yuan, Changyou; Hollingsworth, Rawle I. Letters in Organic Chemistry, 2013 , vol. 10, # 2 p. 77 - 84]

Iridium-catalyzed hydrosilylative reduction of glucose to he...

[Guo, Zhong-Wu; Hui, Yong-Zheng Synthetic Communications, 1996 , vol. 26, # 11 p. 2067 - 2073]

The directed dihydroxylation of allylic alcohols

[Donohoe, Timothy J.; Moore, Peter R.; Waring, Michael J.; Newcombe, Nicholas J. Tetrahedron Letters, 1997 , vol. 38, # 28 p. 5027 - 5030]

The Preparation of 1, 5-Anhydro-D-mannitol (Styracitol) from...

[Fletcher; Diehl Journal of the American Chemical Society, 1952 , vol. 74, p. 3175]

The reduction of acetylated glycopyranosyl bromides to 1, 5-...

[Ness et al. Journal of the American Chemical Society, 1950 , vol. 72, p. 4547]