102208-55-9Relevant academic research and scientific papers
A new synthetic approach to mycobacterial cell wall α-(1→5)-D-arabinofuranosyl C-oligosaccharides
Dondoni, Alessandro,Marra, Alberto
, p. 4067 - 4071 (2007/10/03)
Three designed arabinofuranose building blocks allowed the diastereoselective synthesis of a C-disaccharide and a C-trisaccharide by Wittig olefination. The latter compound represents the first example of all-carbon linked arabinofuranotriose analogue.
First synthesis of methyl α-C-D-arabinofuranosyl-(1→5)-α-D-arabinofuranoside: The C-disaccharide segment of motif C of Mycobacterium tuberculosis
Gurjar, Mukund K.,Nagaprasad, Ravi,Ramana
, p. 7577 - 7579 (2007/10/03)
The synthesis of C-analogue of the disaccharide 2 α-araf-(1→5)-araf, present in motif C of the arabino-galactan portion of Mycobacterium tuberculosis, has been described. The critical C-C bond formation reaction to couple both the furanosyl residues has b
Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp)
McGurk, Philip,Chang, Grace X.,Lowary, Todd L.,McNeil, Michael,Field, Robert A.
, p. 2231 - 2234 (2007/10/03)
The stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro.
Synthesis of Selectively Labeled D-Fructose and D-Fructose Phosphate Analogues Locked in the Cyclic Furanose Form
Persky, Rachel,Albeck, Amnon
, p. 5632 - 5638 (2007/10/03)
2,5-Anhydroglucitol and 2,5-anhydromannitol and their 6-phosphate and 1,6-diphosphate derivatives are cyclic analogues of the α and β anomers of D-fructofuranose, D-fructofuranose-6-phosphate, and D-fructofuranose-1,6-diphosphate. They were synthesized from protected D-mannose or D-glucose. The synthetic method was developed with emphasis on selective 2H labeling of these compounds, as a model for 3H incorporation, which will be used for further biochemical studies. A key cyclization step, based on a benzyl ether nucleophilic attack on an activated alcohol, constructed the ring system. The stereochemistry at C2 (α/β anomers) and at C5 (D sugar) was controlled by selective epimerizations. Mono- and diphosphate analogues were obtained from the same intermediate by changing the sequence of deprotection and phosphorylation steps.
Stereoselective synthesis of tetrahydrofurans and linear methyl enol- ethers from glycals
Bettelli, Enzo,D'Andrea, Piero,Mascanzoni, Stefano,Passacantilli, Pietro,Piancatelli, Giovanni
, p. 221 - 230 (2007/10/03)
The O-benzyl derivatives of 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (D-glucal, 1), 1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (L-rhamnal, 7), and 1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol (D-galactal, 9), underwent stereoselectively a ring contraction by treatment with thallium(III) nitrate (TTN) in MeOH, giving respectively the dimethylacetal derivatives of 3,4,6- tri-O-benzyl-2,5-anhydro-D-mannose, 3,4-di-O-benzyl-6-deoxy-2,5-anhydro-L- mannose (8) and 3,4,6-tri-O-benzyl-2,5-anhydro-D-talose (10). Conversely, the protected glycals 1, 7 and 9, underwent the ring opening reaction by action of the TTN-NaBH4 reagent in MeOH, providing the enantiomerically pure methyl enol-ethers 3,4,6-tri-O-benzyl-2-deoxy-1-O-methyl-D-arabino-hex-1-enitol, 3,4-di-O-benzyl-2,6-dideoxy-1-O-methyl-L-arabino-hex-1-enitol and 3,4,6-tri- O-benzyl-2-deoxy-1-O-methyl-D-lyxo-hex-1-enitol. The perbenzylated glycosyl- glycals, such as 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D- glucopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (cellobial) (16), 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1,5- anhydro-2-deoxy-D-arabino-hex-1-enitol (lactal) (19) and 3,4-di-O-benzyl-6- O-(2, 3,4,6- tetra- O-benzyl- α-D-galactopyranosyl)- 1,5- anhydro-2-deoxy- D-arabino-hex-1-enitol (melibial) (22), showed the same reactivity as the corresponding glycals by reaction with TTN in MeOH, resulting selectively in the ring contracted compounds at the glycal moiety. The reaction with TTN- NaBH4 in MeOH, carried out on 16, 19 and 22, led to the formation of the open chain derivatives at the glycal site.
REACTION BETWEEN GLYCAL BENZYL ETHERS AND THALLIUM(III) NITRATE. SYNTHESIS OF SHOWDOMYCIN ANALOGUES.
Kaye, Andrew,Neidle, Stephen,Reese, Colin B.
, p. 1841 - 1844 (2007/10/02)
On treatment with thallium(III) nitrate, trihydrate in acetonitrile solution, 3,4,6-tri-O-benzyl-D-glucal (5) gives the ring-contracted aldehyde (6) which has been converted into the showdomycin analogue (8) ; 2-(α-D-2'-deoxyribofuranosyl)maleimide (12) h
Stereoselectivity of Electrophile-Promoted Cyclizations of γ-Hydroxyalkenes. An Investigation of Carbohydrate-Derived and Model Substrates
Reitz, Allen B.,Nortey, Samuel O.,Maryanoff, Bruce E.,Liotta, Dennis,Robert, Monahan
, p. 4191 - 4202 (2007/10/02)
We have investigated cyclization reactions of γ-hydroxyalkenes bearing an alkoxy or alkyl substituent on the allylic carbon.A variety of electrophiles N-bromosuccinimide, N-iodosuccinimide, iodine, mercury(II) acetate, mercury(II) trifluoroacetate, mercu
STEREOSELECTIVITY IN THE ELECTROPHILE-MEDIATED CYCLIZATION OF 2,3,5-TRI-O-BENZYL-1,2-DIDEOXY-D-arabino-HEX-1-ENITOL. A STEREOCONTROLLED SYNTHESIS OF 1-AMINO-2,5-ANHYDRO-3,4,6-TRI-O-BENZYL-1-DEOXY-D-GLUCITOL
Freeman, Fillmore,Robarge, Kirk D.
, p. 1 - 12 (2007/10/02)
Cyclization of 2,3,5-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enitol (2) with mercuric acetate, mercuric trifluoroacetate, iodine, and N-bromosuccinimide gave preponderantly the allo isomer of the C-arabinofuranosyl structure. 1-Amino-2,5-anhydro-3,4,6-tr
