50600-39-0Relevant articles and documents
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.
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.
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.