118013-56-2Relevant academic research and scientific papers
Stereoselective synthesis of a novel natural carbasugar and analogues from hydroxymethylated cycloalkenone scaffolds
Rej, Rohan,Jana, Navendu,Kar, Shantasree,Nanda, Samik
, p. 364 - 372 (2012/07/16)
Novel carbasugars from Streptomyces lincolnensis have been synthesized from an enantiomerically pure 5-hydroxymethyl-cyclohex-2-enone scaffold via a stereoselective approach. Several structural analogues of those carbasugars have also been synthesized in a stereoselective manner from hydroxymethylated cycloalkenone derivatives.
A convenient approach for access to both carbapentofuranoses and carbahexopyranoses. Stereocontrolled synthesis of enantiopure Carba-D-ribofuranoses, Carba-D-arabinofuranoses and Carba-L-gulopyranose
Ghosh, Subrata,Bhaumik, Tanurima,Sarkar, Niladri,Nayek, Abhijit
, p. 9687 - 9694 (2007/10/03)
A new approach to carbasugars in enantiomerically pure form is reported. The key step involves ring-closing metathesis of dienols 6 derived from a (R)-(+)-glyceraldehyde derivative 4 to form the substituted cyclopentenol 9 and cyclohexenol 34a. Stereocont
Variable strategy toward carbasugars and relatives. 2. Diversity-based synthesis of β-D-xylo, β-D-ribo, β-L-arabino, and β-L-lyxo 4a-carbafuranoses and (4a-carbafuranosyl)thiols
Rassu, Gloria,Auzzas, Luciana,Pinna, Luigi,Zambrano, Vincenzo,Battistini, Lucia,Zanardi, Franca,Marzocchi, Lucia,Acquotti, Domenico,Casiraghi, Giovanni
, p. 8070 - 8075 (2007/10/03)
The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-β-D-xylofuranose, 4a-carba-β-D-ribofuranose, 4a-carba-β-L-arabinofuranose, and 4a-carba-β-L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-β-D-xylofuranosyl)thiol, (4a-carba-β-D-ribofuranosyl)thiol, (4a-carba-β-L-arabinofuranosyl)thiol, and (4a-carba-β-L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.
Synthesis of all stereoisomeric carbapentofuranoses
Marschner,Baumgartner,Griengl
, p. 5224 - 5235 (2007/10/02)
All carbocyclic analogs of the pentofuranoses were synthesized starting from norborn-5-en-2-one (1). By using either base- or acid-catalyzed Baeyer- Villiger reaction of 1, the central intermediates 2 and 3 were obtained. The required functionalization of the olefinic double bond was achieved either by cis-hydroxylation in the case of the ribo, lyxo, and α-xylo derivatives or by epoxidation and subsequent opening with aqueous perchloric acid. In the latter case, a pronounced selectivity for opening the epoxy alcohol in the 3- position was found. I an epoxy acetate with both functions on the same side of the ring was used, the eposide was opened in the 2-position by neighboring group participation of the acetate. The requisite side chain degradation was accomplished either by conversion of the ester into an olefin and subsequent dihydroxylation/cleavage reaction or by Curtius rearrangement to the amine and its conversion into an acetate.
BIOSYNTHESIS OF ARISTEROMYCIN: EVIDENCE FOR THE INTERMEDIACY OF A 4β-HYDROXYMETHYL-1α,2α,3α-TRIHYDROXYCYCLOPENTANETRIOL.
Parry, Ronald J.,Haridas, Kochat,Jong, Randall De,Johnson, Carl R.
, p. 7549 - 7552 (2007/10/02)
Evidence for the intermediacy of a 4β-hydroxymethyl-1α,2α,3α-trihydroxycyclopentanetriol (5 or 6) in the biosynthesis of the nucleoside antibiotic aristeromycin (1) has been obtained by administration of doubly-labeled forms of D-glucose to the fermentation broth of Streptomyces citricolor followed by trapping of the tetrol 5 using isotope dilution methods.
Synthesis of α- and β-D-carbaribofuranose from (+)-norborn-5-en-2-one
Marschner, Christoph,Penn, Gerhard,Griengl, Herfried
, p. 2873 - 2874 (2007/10/02)
α- and β-D-carbaribofuranose 7 and 9, resp., are prepared from ( + )-norborn-5-en-2-one in a 6-step (8-step, resp.) synthetic sequence in 27% (13%, resp.) overall yield.
Syntheses of (1S,2S,3S,4R)- and (1R,2R,3S,4R)-2,3,4-Trihydroxycyclopentane-1-methanol, Carbocyclic Analogues of α-L-Arabinofuranose and β-D-Ribofuranose
Tadano, Kin-ichi,Hakuba, Ken,Kimura, Hiroshi,Ogawa, Seiichiro
, p. 276 - 279 (2007/10/02)
The title compounds, two carbocyclic analogues of aldopentofuranoses, were synthesized from D-glucose.The key cyclopentane ring formation was achieved under the glycol cleavage reaction of methyl 3-O-benzyl-5,6-dideoxy-6-C-(methoxycarbonyl)-D-xylo-hepto-1
A Novel Transformation of Four Aldoses to Some Optically Pure Pseudohexopyranoses and a Pseudopentofuranose, Carboxylic Analogues of Hexopyranoses and Pentofuranose. Synthesis of Derivatives of (1S,2S,3R,4S,5S)-, (1S,2S,3R,4R,5S)-, (1R,2R,3R,4R,5S)-, (1S,
Tadano, Kin-ichi,Maeda, Hiroo,Hoshino, Masahide,Iimura, Youichi,Suami, Tetsuo
, p. 1946 - 1956 (2007/10/02)
Knoevenagel reactions with dimethyl malonate of the suitably protected acylic aldehydes 6, 20, 34, and 46, which were prepared from D-ribose, D-xylose, D-arabinose, and D-erythrose, respectively, proceeded smoothly to provide α,β-unsaturated diesters 7, 2
