20196-70-7Relevant academic research and scientific papers
Diastereoselective Construction of the 6-Oxa-2-azabicyclo[3.2.1]octane Scaffold from Chiral α-Hydroxyaldehyde Derivatives by the Aza-Prins Reaction
Mahía, Alejandro,Badorrey, Ramón,Gálvez, José A.,Díaz-De-Villegas, María D.
, p. 8048 - 8057 (2017)
(R)-2,3-Di-O-benzylglyceraldehyde and N-tosyl homoallylamine undergo aza-Prins cyclization to afford (1R,5S,7S)-7-[(benzyloxy)methyl]-2-tosyl-6-oxa-2-azabicyclo[3.2.1]octane in a highly diastereoselective manner through an unexpected intramolecular nucleophilic attack. Our work has opened a new route toward the asymmetric synthesis of 7-(alkyl or aryl)-6-oxa-2-azabicyclo[3.2.1]octane derivatives from chiral α-hydroxyaldehyde derivatives in one step.
A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides
Miller, Gavin J.,Broberg, Karl. R.,Rudd, Claire,Helliwell, Madeleine R.,Jayson, Gordon C.,Gardiner, John M.
supporting information, p. 11208 - 11219 (2015/11/27)
d-Glucosamine derivatives bearing latent O4 functionality provide modified H/HS-type disaccharide donors for a final stage capping approach enabling introduction of conjugation-suitable, non-reducing terminal functionality to biologically important glycosaminoglycan oligosaccharides. Application to the synthesis of the first O4-terminus modified synthetic LMWH decasaccharide and an HS-like dodecasaccharide is reported.
A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin
Kadota, Isao,Abe, Takashi,Uni, Miyuki,Takamura, Hiroyoshi,Yamamoto, Yoshinori
, p. 3643 - 3647 (2008/09/20)
Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring.
Total synthesis of (-)-Pramanicin
Aoki, Shin-ya,Tsukude, Taro,Miyazaki, Yukari,Takao, Ken-ichi,Tadano, Kin-ichi
, p. 49 - 54 (2008/02/08)
The total synthesis of natural (-)-pramanicin, a highly oxygenated γlactam-type antifungal agent, is described. The enantiospecific total synthesis of this natural product commenced with 5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose as an enantiopure star
Selectivity guidelines and a reductive elimination-based model for predicting the stereochemical course of conjugate addition reactions of organocuprates to γ-alkoxy-α,β-enoates
Kireev, Artem S.,Manpadi, Madhuri,Kornienko, Alexander
, p. 2630 - 2640 (2007/10/03)
Current models used to predict the stereochemical outcome of organocopper conjugate addition processes focus on the nucleophilic addition step as stereochemistry-determining. Recent kinetic, NMR, kinetic isotope effect, and theoretical density functional
Cysteine protease inhibitors
-
, (2008/06/13)
of the formula (IV): where: R1=R′C(O), R′SO2, R′=a bicyclic, saturated or unsaturated, 8-12 membered ring system containing 0-4 hetero atoms selected from S, O and N, which is optionally substituted with up to four substituents independently selected from groups a), b) and c) below; or R′=a monocyclic, saturated or unsaturated, 5-7 membered ring containing 0-3 hetero atoms selected from S, O and N, which monocyclic ring bears at least one substituent selected from group a) and/or c) and which may optionally bear one or two further substituents selected from group b); R4=H, C1-7-alkyl, Ar-C1-7-alkyl, Ar, C3-7-cycloalkyl; C2-7alkenyl; R3=C1-7-alkyl, C2-C7 alkenyl, C2-C7 alkenyl, C3-7-cycloalkyl, Ar-C1-7-alkyl, Ar; R5=C1-7-alkyl, halogen, Ar-C1-7-alkyl, C1-3-alkyl-CONR3R4 or a bulky amine R6 is H, C1-7-alkyl, Ar-C1-7-alkyl, C1-3-alkyl-SO2-Rix, C1-3-alkyl-C(O)—NHRix or CH2XAr q is 0 or 1 have utility as inhibitors of cysteine proteases such as cathepsin K and falcipain.
The stereospecific synthesis of mixed-acid phospholipids with polyunsaturated fatty acid from D-mannitol
Xia, Jie,Hui, Yong-Zheng
, p. 451 - 458 (2007/10/03)
The polyunsaturated mixed-acid phosphatidylcholine, 1-palimoyl-2-linolenoyl-sn-glycerophosphocholine 1a and 1-stearoyl-2-linolenoyl-sn-glycerophosph 1b prepared from D-mannitol as an optically active starting material is described.
Synthesis and antiherpetic activity of (S)-, (R)- and (±)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine, linear isomers of 2'-nor-2'-deoxyguanosine
Ashton,Canning,Reynolds,Tolman,Karkas,Liou,Davies,DeWitt,Perry,Field
, p. 926 - 933 (2007/10/02)
Racemic 9-[2,3-dihydroxy-1-propoxy)methyl]guanine [(±)-iNDG], a new analogue of acyclovir (ACV) and a structural analogue of 2'-nor-2'-deoxyguanosine (2'NDG), was synthesized and found to inhibit the replication of herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). Subsequently, its optical isomers, (R)- and (S)-iNDG, were prepared from chiral intermediates. The chloromethyl ethers of 1,2-di-O-benzyl-D- and -L-glycerol were made and reacted with tris(trimethylsilyl)guanine to give the 9-alkylated guanines, which were deprotected by catalytic hydrogenolysis. Against HSV-1 and HSV-2 in cell culture, (S)-iNDG was approximately 10- to 25-fold more active than the R enantiomer and had an ED50 comparable to those for ACV and 2'NDG. The inferior activity of (R)-iNDG paralleled the poor inhibition of viral DNA polymerase by its phosphorylation products. In mice infected intraperitoneally or orofacially with HSV-1 or intravaginally with HSV-2, (S)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine [(S)-iNDG] was less efficacious than 2'NDG but comparable to or more active than ACV.
