50600-39-0Relevant academic research and scientific papers
Dual course of bisacetonation of D-xylose in a system Me 2CO-Me2C(OMe)2-H2SO4
Khasanova,Selezneva,Gimalova,Miftakhov
experimental part, p. 762 - 765 (2009/10/04)
In the course of formation of a bisisopropylidene protective group by keeping D-xylose in a mixture Me2CO-(MeO)2CMe 2-H2SO4 alongside the expected 1,2:4,5-O-diisopropylidene derivative formed minor dimethylacetal, 2,3:4,5-O-diisopropylidene-D-xylose, inseparable from the main product by the chromatography on SiO2. The conditions were found for the selective formation and isolation of the latter, some its one-pot transformations were studied resulting in synthetically promising orthogonally protected acyclic C5-synthons.
[2+2]-Cycloaddition of chlorosulfonyl isocyanate to (Z)-propenyl ethers bound to polystyrene resins by alkylsulfonyl linkers
Lysek, Robert,Grzeszczyk, Barbara,Furman, Bartlomiej,Chmielewski, Marek
, p. 4177 - 4187 (2007/10/03)
The 3-O- and 5-O-(Z)-propenyl ethers derived from 1,2-O-isopropylidene- α-D-xylo- and glucofuranoses, respectively, were attached to the Merrifield, MPPC and NCPSC resins using alkylsulfonyl linkers. The [2+2]-cycloaddition of chlorosulfonyl isocyanate to
Synthesis of nucleosides from 4-methylidenefuranoses: A non-classical electrophilic addition
Robles, Rafael,Izquierdo, Isidoro,Rodriguez, Concepcion,Plaza, Maria T.,Mota, Antonio J.,Alvarez de Cienfuegos, Luis
, p. 399 - 405 (2007/10/03)
The reaction of persilylated bases (thymine, uracil, cytosine, and 5-fluorouracil) with either 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-erythro-pent-4-enofuranose 6 or its 3-O-benzyl analogue 7 in the presence of N-iodosuccinimide (NIS) afforded two types of product with high stereoselectivity; either (1′S,2′R,3′S)-3′-O-benzoyl- 8-10 or -3′-O-benzyl-5′-deoxy-5′-iodo-1′,2′-O- isopropylidene-4′-oxo-1′-yl-pyrimidines 11-13, respectively, from 1,4-addition with participation of the oxygen atom at the furanoid ring, and either 3′-O-benzoyl- 14-16, or 3′-O-benzyl-5′-deoxy-5′-iodo-1′,2′-O- isopropylidene-β-L-lyxo-4′-yl-pyrimidine and 17-19 resulting from normal electrophilic addition at the exocyclic methylene group. A third compound was isolated from the reaction of 7 with persilylated uracil/NIS and identified as the doubly N,N′-glycosylated pyrimidine 20.
Methyl 5-deoxy-α and β-D-xylofuranosides
Moravcova, Jitka,Capkova, Jindra,Stanek, Jan,Raich, Ivan
, p. 1061 - 1073 (2007/10/03)
Synthesized from D-xylose, methyl 5-deoxy-α-D-xylofuranoside (1) and methyl 5-deoxy-β-D-xylofuranoside (2) were obtained in overall yields of 24 and 26 %, respectively. The key step in the synthesis was the separation of an anomeric mixture on a strong an
Regiocontrolled formation of iodohydrins and epoxides from Vic-diols
Adiyaman,Khanapure,Hwang,Rokach
, p. 7367 - 7370 (2007/10/02)
A novel method for the stereoselective preparation of iodohydrins and epoxides from stereogenic vicinal diols is described. This new high-yield methodology consists of the conversion of thionocarbonates such as 12 to the primary iodo derivative 14 with complete regiocontrol. Deprotection of ther secondary alcohol derivative in 14 gives the corresponding synthetically versatile iodohydrin 16, which is converted to epoxide 17. This methodology has been applied to complex tetraols 29 and 34. In the case of diols the transformation is conveniently carried out in high yield as a one-pot reaction.
Short Synthetic Route to Congeners of the Undecose Antibiotic Herbicidin
Bearder, John R.,Dewis, Mark L.,Whiting, Donald A.
, p. 227 - 234 (2007/10/02)
The undecose backbone of the herbicidins has been assemled via direct alkylation, hydroxyalkylation, or acylation of the cyclic vinylanion 5 with the xylofuranose triflate 14, aldehyde 6, or acid chloride 10, respectively.
APPLICATION OF THE KECK RADICAL COUPLING REACTION TO THE PREPARATION OF ALLYLATED C5 FURANOSIDES AND C6 PYRANOSIDES
Mootoo, David,Wilson, Phyllis,Jammalamadaka, Vasu
, p. 841 - 850 (2007/10/02)
Allylated C5 furanosides and C6 pyranosides were prepared from known monosaccharide diol or polyol derivatives via a reaction sequence involving the initial selective formation of the primary iodide followed by application of the Keck allyl radical coupling reaction.Although the yields of the products in the coupling reaction were somewhat modest (usually 55-65percent), the protocol was applicable to a variety of substrates, including sterically crowded cases, is experimentally simple and suitable for large scale preparations.
A Concise And General Entry into (R)-4-Hydroxy-2-Substituted Cyclopent-2-enones from D-Glucose: Chiral Intermediates for the Synthesis of PGE2, (-)-Pentenomycin I, and Allethrin
Achab, Said,Das, Bhupesh C.
, p. 2863 - 2873 (2007/10/02)
A general strategy for the transformation of D-glucose into different (R)-4-hydroxycyclopent-2-enones is described.This has been illustrated by the synthesis of (R)-2--4-hydroxycyclopent-2-enone, (R)-2-benzyloxymethyl-4-hydroxycyclopent-2-enone, and (R)-2-allyl-4-hydroxycyclopent-2-enone, which are potential chiral synthons for prostaglandin E2, the antibiotic (-)-pentenomycin I, and the synthetic insecticide allethrin, respectively.The second chiral synthon was obtained by two different routes, one of them involving a novel palladium(0)-catalysed rearrangement of a vinyloxirane intermediate.
5-Deoxy-3-O-thienylmethyl or furylmethyl-1,2-O-alkylidene-alpha-D-xylofuranose herbicide derivatives
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, (2008/06/13)
5-Deoxy-3-O-thienylmethyl or furylmethyl-1,2-O-alkylidene-alpha-D-xylofuranose and 5-C-alkyl, alkylidene and alkenyl derivatives thereof. The compounds are useful as herbicides and plant growth regulators.
