196397-53-2Relevant articles and documents
Gram-scale synthesis of an armed colitose thioglycoside
Lloyd, Dina,Bennett, Clay S.
, p. 9826 - 9829 (2014)
A concise gram-scale synthesis of protected colitose thioglycosides for use in bacterial carbohydrate antigen synthesis is described. The synthesis proceeds in six steps and 59-70% overall yield from commercially available L-fucose, making it the most eff
Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions
Dong, Hai,Feng, Guang-Jing,Guo, Yang-Fan,Liu, Chun-Yang,Luo, Tao
, (2022/02/07)
A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.
Acylation of carbohydrates over Al2O3: Preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides
Tiwari, Pallavi,Misra, Anup Kumar
, p. 339 - 350 (2007/10/03)
Selective and per-O-acylation of carbohydrate derivatives using acyl chlorides and Al2O3, a solid support reagent, is reported. This protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.
Synthesis of fully protected α-l-fucopyranosyl-(1→2)-β-d- galactopyranosides with a single free hydroxy group at position 2′, 3′ or 4′ using O-(2-naphthyl)methyl (NAP) ether as a temporary protecting group
Szabo, Zoltan B.,Borbas, Aniko,Bajza, Istvan,Liptak, Andras
, p. 83 - 95 (2007/10/03)
Perbenzylated methyl α-l-fucopyranosyl-(1→2)-β-d- galactopyranosides having a single free OH group at position C-2′, C-3′ or C-4′ have been synthesized. Methyl 3,4,6-tri-O-benzyl- β-d-galactopyranoside was glycosylated either with phenyl 3,4-di-O-benzyl-2
Stereocontrolled elaboration of natural (-)-polycavernoside A, a powerfully toxic metabolite of the red alga Polycavernosa tsudai
Paquette, Leo A.,Barriault, Louis,Pissarnitski, Dmitri,Johnston, Jeffrey N.
, p. 619 - 631 (2007/10/03)
A stereoselective total synthesis of natural levorotatory polycavernoside A (1) has been achieved. Initial investigations produced the properly activated disaccharide unit 18b via the conjoining of building blocks originating from L-fucose and D-xylose. T