190779-65-8Relevant academic research and scientific papers
Synthesis and absolute structures of Mycoplasma pneumoniae β-glyceroglycolipid antigens
Miyachi, Akira,Miyazaki, Atsushi,Shingu, Yuko,Matsuda, Kazuhiro,Dohi, Hirofumi,Nishida, Yoshihiro
experimental part, p. 36 - 43 (2011/03/20)
Just recently, a pair of β-glycolipids was isolated from the cell membrane of Mycoplasma pneumoniae as a mixture of the two compounds. They are the major immunodeterminants of this pathogenic Mycoplasma and indicate high medicinal potential. They have a β
Strategies for the formation of 1-dethia-1-oxa-cephams
Kaluza,Furman,Krajewski,Chmielewski
, p. 5553 - 5562 (2007/10/03)
The paper describes three possible routes for the formation of 1-dethia-1-oxa-cephams. The first two routes: (a) [2+2]cycloaddition to chiral vinyl ethers and (b) condensation of 4-acetoxyazetidin-2-one to chiral alcohols, are followed by the ring closure step involving N-alkylation. The third route (c) consists of N-alkylation prior to the cyclization step. In order to compare routes (a), (b) and (c), diastereomeric 1-dethia-3-(4-methoxybenzyloxy)-1-oxacephams were synthesized using three possible strategies. While the comparison of stereoselectivities of the [2+2]cycloaddition method (a) and the condensation (b) shows unequivocally the advantage of the former, the route (c) leads to the reverse direction of asymmetric induction relative to the first two steps and offers the highest asymmetric induction. (C) 2000 Elsevier Science Ltd.
Synthesis of 3',4'-bisphosphate-containing analogs of adenophostin A
Van Straten, Nicole C. R.,Kriek, Nicole M. A. J.,Cziria, Zsolt A. C.,Van der Marel, Gijsbert A.,Van Boom, Jacques H.
, p. 6539 - 6554 (2007/10/03)
Glycosylation of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α/β-D-glucopyranoside (6) with tert-butyldiphenylsilylglycol (7) or 1,2-di-O-p-methoxybenzyl-sn-glycerol (16) under the agency of N-iodosuccinimide/triflic acid afforded α-glucosides 8 and 17, respectively. Protective group manipulations (8 → 10 and 17 → 20) and acetolysis of the methylthiomethyl functions yielded 2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-1- (11) and 3-0-(3,4,6-tri-O-acetyl-2-O-benzyl -α-D-glucopyranosyl)-2-O-acetoxymethyl-1-O-tert-butyldiphenylsilyl-sn-glycerol (21). Vorbruggen condensation with silylated 6-N-benzoyladenine (22), subsequent protective group manipulations on 23 and 29 followed by phosphorylation furnished, after purification, homogeneous glycol-based adenophostin A analog 4 and glycerol-based analog 5.
