113299-30-2Relevant academic research and scientific papers
Synthesis of 4a-carba-β-l-lyxofuranose, 4a-carba-β-l- arabinofuranose and 2,2,5-trimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one using Mn/CrCl3 mediated domino reactions and ring closing metathesis
Mishra, Girija Prasad,Kumar, Bejugam Santhosh,Venkateswara Rao, B.
, p. 1161 - 1169,9 (2020/09/09)
A common method for the synthesis of 4a-carba-β-l-lyxofuranose and 4a-carba-β-l-arabinofuranose from d-mannose and 2,2,5-trimethyl-3a,6a- dihydro-cyclopenta[1,3]dioxol-4-one from d-ribose is described using catalytic Nozaki-Hiyama-Kishi (NHK) conditions and ring closing metathesis (RCM). In this transformation, ω-deoxy-ω-iodo manno/ribo furanoside undergoes reductive elimination in the presence of Mn/CrCl3 to give the corresponding olefin-aldehyde which was trapped by nucleophile under the same conditions to afford the desired diolefinic species. The ring closing metathesis reaction on these diolefinic species with Grubbs second generation catalyst produced the required carbocycles.
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.
Transformation of D-Erythrose to Some Pseudoaldopentofuranoses. Syntheses of (1S,2R,3S,4S)-, (1R,2R,3S,4S)-, and (1R,2S,3S,4S)-2,3,4-Trihyroxy-1-(hydroxymethyl)cyclopentanes and (1R,2S,3R,4R)-2,3-Dihydroxy-4-(hydroxymethyl)-1-cyclopentanamine
Tadano, Kin-ichi,Hoshino, Masahide,Ogawa, Seiichiro,Suami, Tetsuo
, p. 1427 - 1432 (2007/10/02)
Sodium borohydride reduction of (1S,3S,4S)-1--3,4-(isopropylidenedioxy)-2-cyclopentanone (11), which was prepared from D-erythrose, proceeds exlusively from the β-face to provide 2R-hydroxyl derivative 12.Compound 12 is a derivative of carbocyclic analogue of β-L-lyxofuranose.Silica gel promoted configurational inversion at the branched carbon in 11 followed by sodium borohydride reduction provides 1R,2R diastereomer 17 and 12 a 2.8:1 ratio.The former is a protected form of carboxylic α-D-ribofuranose.Replacement of the mesyloxy group in 23, which was derived from 17, by a hydroxyl group in a SN2 fashion and deprotection of the product followed by acetylation gave a derivative of carbocyclic α-D-xylofuranose 24.Compound 17 was also converted to compound 7, a key intermediate for the synthesis of the carboxylic nucleoside antibiotic (-)-aristeromycin (1), via a SN2 replacement of the mesyloxy group in 26 by an azide group.
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
