343338-29-4Relevant academic research and scientific papers
A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides
Balmond, Edward I.,Benito-Alifonso, David,Coe, Diane M.,Alder, Roger W.,McGarrigle, Eoghan M.,Galan, M. Carmen
supporting information, p. 8190 - 8194 (2014/08/18)
A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.
Stereocontrolled total synthesis of polygalolide A
Yamada, Hitomi,Adachi, Masaatsu,Isobe, Minoru,Nishikawa, Toshio
supporting information, p. 1428 - 1435 (2013/07/26)
The total synthesis of polygalolide A, a secondary metabolite that was isolated from a Chinese medicinal plant, is reported. A key issue in this synthesis was construction of an oxabicyclo[3.2.1] skeleton, which was solved by the development of an intramo
Total synthesis of polygalolide A
Adachi, Masaatsu,Yamada, Hitomi,Isobe, Minoru,Nishikawa, Toshio
supporting information; experimental part, p. 6532 - 6535 (2012/02/15)
The total synthesis of polygalolide A was accomplished through intramolecular C-glycosylation of glucal modified with siloxyfuran. The siloxyfuran group and siloxy substituent at the C-3 position played crucial roles in allowing direct access to the highl
One-pot conversion of glycals to cis-1,2-isopropylidene-α-glycosides
Lohman, Gregory J. S.,Seeberger, Peter H.
, p. 7541 - 7543 (2007/10/03)
Described is a general method for the conversion of glycals to the corresponding 1,2-cis-isopropylidene-α-glycosides. Epoxidation of glycals with dimethyldioxirane followed by ZnCl2-catalyzed addition of acetone converted a variety of protected glycals into 1,2-cis-isopropylidene-α-glycosides in good yield. The reaction is compatible with a range of protecting groups, including esters, benzyl ethers, and silyl ethers, as well as free hydroxyl groups. This method has been applied to develop a synthesis of protected glucuronic acid 1, a key intermediate in the synthesis of glycosaminoglycans. Compound 1 was produced in seven steps and 32% overall yield.
