1092103-69-9Relevant academic research and scientific papers
A convenient synthesis of carbohydrate derived furo/pyrano[2,3-b]pyrans from 2-hydroxymethyl glycals
Chalapala, Sudharani,Bandi, Ramakrishna,Bhumireddy Chinnachennaiahgari, Venkatesh,Perali, Ramu Sridhar
, p. 3923 - 3931 (2017)
An efficient method for the stereoselective synthesis of various linearly fused bicyclic acetals using 2-hydroxymethyl glycals, involving Ferrier type rearrangement and ring-closing metathesis as the key steps, is revealed. The methodology was shown to be very general by applying it to various sugar substrates which lead to the formation of various bicyclic furo/pyrano[2,3-b]pyran ring systems.
Stereoselective synthesis of 2-C-methylene glycosides and disaccharides via direct allylic substitution of hydroxy group in benzylated glycals
Nagaraj, Paramathevar,Ramesh, Namakkal G.
scheme or table, p. 599 - 604 (2010/09/05)
InCl3 efficiently catalyzes allylic substitution of the hydroxy group of 2-C-hydroxymethyl glycals to afford a diversity of 2-C-methylene alkyl and aryl glycosides as well as disaccharides in high yields. This protocol surpasses the existing methods for the synthesis of 2-C-methylene glycosides as it obviates the need for functionalizing the allylic hydroxy group of glycals. The interest of this methodology relies on the extremely mild conditions required even with a free hydroxyl group at the allylic position of the glycals and that too only with a catalytic amount of InCl3. The reaction is fast (30 min.), stereoselective and is compatible with a variety of oxygenated nucleophiles including those possessing acid-labile groups. A mechanistic investigation on the direct formation of an α,α-(1→1)linked disaccharide derivative from 2-C-hydroxymethyl galactal reveals that the reaction proceeds through a domino Ferrier rearrangement followed by a facile 1,3-alkoxy migration.
InCl3-catalyzed rapid 1,3-alkoxy migration in glycal ethers: Stereoselective synthesis of unsaturated α-O-glycosides and an α,α-(1→1)-linked disaccharide
Nagaraj, Paramathevar,Ramesh, Namakkal G.
experimental part, p. 4607 - 4614 (2009/04/11)
InCl3 catalyzes a facile stereoselective 1,3-migration of allylic ethers of glycals to afford 2-C-methylene- and 2,3-unsaturated-α- O-glycosides in high yields. The reaction is rapid (10 min), requires only 20 mol-% of the catalyst, and is compatible with acid-labile functional groups such as epoxides and acetals. This methodology provides a convenient alternative to the Ferrier rearrangement. A direct synthesis of an α,α-(1→1)- linked disaccharide derivative by a domino process is also reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
