848844-44-0Relevant articles and documents
Stereoselective glycosylation of d-galactals by diethyl phosphorochloridite- and AlCl3-assisted Ferrier rearrangement
Chen, Yen-Bo,Wang, Su-I.,Lin, Zi-Ping,Lin, Chun-Hung,Hsieh, Min-Tsang,Lin, Hui-Chang
, p. 350 - 358 (2015)
α-2,3-Unsaturated galactosides were synthesized in good to excellent yields by the initial activation of d-galactals with diethyl phosphorochloridite and the subsequent glycosyl addition via Ferrier rearrangement with various O-nucleophiles in the presenc
2,3-unsaturated allyl glycosides as glycosyl donors for selective α-glycosylation
Kumar, Brijesh,Aga, Mushtaq A.,Rouf, Abdul,Shah, Bhahwal A.,Taneja, Subhash C.
supporting information; experimental part, p. 3506 - 3510 (2011/06/26)
In the presence of NBS and a catalytic amount of a Lewis acid, 2,3-unsaturated allyl glycosides [6-(allyloxy)-3,6-dihydro-2-(hydroxymethyl)-2H- pyran-3-ol] have been successfully used as versatile glycosyl donors for the stereoselective α-glycosylation of
Montmorillonite K-10 clay-catalyzed Ferrier rearrangement of 2-C-hydroxymethyl-D-glycals, 3,4,6-tri-O-alkyl-D-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol: A few unexpected domino transformations
Kumaran, Elumalai,Santhi, Meenakshisundaram,Balasubramanian, Kalpattu K.,Bhagavathy, Shanmugasundaram
experimental part, p. 1654 - 1661 (2011/11/06)
Montmorillonite K-10 clay-catalyzed substitution reactions of 3,4,6-tri-O-alkyl-2-C-hydroxymethyl-Dglycals, 3,4,6-tri-O-acetyl-D-glycals, 3,4,6-tri-O-alkyl-D-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol with a few alcohols and phenols are described. The reactions of 2-C-hydroxymethyl-D-glycals with phenols were similar to those of 2-C-acetoxymethyl-D-glycals and afforded pyrano[2,3-b]benzopyrans. This montmorillonite K-10 clay-catalyzed transformation is facile both under ambient (Method 1) and microwave conditions (Method 2). Ferrier rearrangement of 3,4-(dihydro-2H-pyran-5-yl)methanol with p-cresol, 2,6-xylenol, and ethanol led to totally unexpected transformations. Reaction of 2-C-hydroxymethyl- D-galactal with 2,6-dimethylphenol in the presence of montmorillonite K-10 led to a novel domino transformation affording 4-(5',6'-dihydro-4H-pyran-3'-ylmethyl)-2,6-dimethylphenol. In contrast, 3,4,6-tri-O-acetyl-D-glucal furnished the Ferrier rearrangement product, 2,6-dimethylphenyl 4,6-di-Oacetyl- 2,3-dideoxy-α-D-erythro-hex-2- enopyranoside. Also, isomerization of 3,4,6-tri-O-alkyl-D-glycals to products of allylic rearrangement, 2,3-unsaturated-O-glycosides in good yields is reported.
The use of ultrastable y zeolites in the Ferrier rearrangement of acetylated and benzylated glycals
Levecque, Pieter,Gammon, David W.,Jacobs, Pierre,De Vos, Dirk,Sels, Bert
experimental part, p. 828 - 835 (2010/09/08)
The Ferrier rearrangement of a selection of protected glycals was successfully performed using a commercially available H-USY zeolite CBV-720 as catalyst, selected after screening a range of similar catalysts. By incorporating either alcohols, thiophenol, trimethylsilyl azide or allyltrimethylsilane in the reaction it was shown that a range of O-, S-, N- and C-glycosides could be formed. With benzylated glucal and galactal in particular, use of the CBV-720 catalyst led to significantly higher yields of the 2,3-dehydroglycosides than previously reported.
Direct Ferrier rearrangement on unactivated glycals catalyzed by indium(III) chloride
Nagaraj, Paramathevar,Ramesh, Namakkal G.
supporting information; experimental part, p. 3970 - 3973 (2009/10/04)
Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient
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.
