106357-04-4Relevant academic research and scientific papers
Stereoselective Oxylactonization. Preparation of 2-Deoxy-DL-ribono-1,4-lactone Derivatives from 3-Silyloxy-4-alkenamides
Ichikawa, Yuch-ichiro,Miwa, Tetsuo,Narasaka, Koichi
, p. 3309 - 3311 (1985)
The oxylactonization of 3-silyloxy-4-alkenamides proceeds stereoselectively by treatment with m-chloroperbenzoic acid to give the corresponding 2-deoxy-DL-ribono-1,4-lactone derivatives.
SYNTHESIS OF 2-DEOXYXYLOLACTONE FROM GLYCEROL DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE CARBON-HYDROGEN INSERTION REACTIONS
Doyle, Michael P.,Dyatkin, Alexey B.,Tedrow, Jason S.
, p. 3853 - 3856 (1994)
diazodecomposition of 1,3-dialkoxy-2-propyl diazoacetates catalyzed by chiral dirhodium(II) carboxamides results in highly enantioselective and diastereoseelctive carbon-hydrogen insertion which forms 3,5-dialkyl 2-deoxyxylolactones in up to 98percent enantiomeric excess.
Stereocontrol in organic synthesis using silicon-containing compounds. Syntheses of (±)-2-deoxyribonolactone and (±)-arabonolactone
Fleming, Ian,Ghosh, Sunil K.
, p. 2711 - 2720 (2007/10/03)
Samarium iodide reacts with methyl (Z)-3-dimethyl(4-methylphenyl)silylprop-2-enoate 5b to give dimethyl (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]hexane-1,6-dioate 8b with high stereoselectivity. This meso diester can be converted into (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]pentan-5-olide 16 by Dieckmann cyclisation, demethoxycarbonylation and Baeyer-Villiger reaction. Silyl-to-hydroxy conversion and relactonisation gave (±)-deoxyribonolactone, and anti-selective enolate hydroxylation followed by silyl-to-hydroxy conversion gave (±)-arabonolactone. An attempt to synthesise sugars with the relative configuration (3RS,4RS) was thwarted by an unprecedented retention of configuration at the migration origin in the cationic rearrangement of (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]-5-hydroxypentanoic acid 28 to (3RS,4SR)-3,5-bis[dimethyl(4-methylphenyl)silyl]pentan-1,4-olide 30.
Stereospecific 1,2-Silyl Shift in a Cationic Rearrangement with Retention of Configuration at the Migration Origin
Fleming, Ian,Ghosh, Sunil K.
, p. 1777 - 1779 (2007/10/02)
Mitsunobu reaction on the hydroxy acids 5 and 10 stereospecifically gave the lactones 7 and 4, respectively, with retention of configuration at C-4.
REACTION OF METHYL DIAZOACETATE WITH 2,3 O-ISOPROPYLIDENE-D-GLYCERALDEHYDE. STEREOSELECTIVITY IN THE SYNTHESIS OF 2-DEOXY-D-ALDONATES AND 2-DEOXY-γ,D-ALDONOLACTONES.
Lopez-Herrera, Fidel J.,Valpuesta-Fernandez, Maria,Garcia-Claros, Salvador
, p. 7165 - 7174 (2007/10/02)
The reaction of 2,3-O-isopropylidene-D-glyceraldehyde with diazoacetates are revised.In the absence of catalyst, the methyl (3S,4R) and (3R,4R)-4,5-O-isopropylidene-2-diazo-3,4,5-trihydroxypentanoate (4a and 4b) were the new and main products in a high stereoselective reaction (84:16).These products were easily converted into the corresponding 2-deoxy-3-ulosonates (3), 2-deoxy-aldonates (6,7 and 8) and 2-deoxy-γ,D-aldonolactones (9 and 10).
EFFICIENT SYNTHESIS OF (S)-5-HYDROXYMETHYL-5(H)-FURAN-2-ONE FROM D-MANNITOL
Danilova, G. A.,Mel'nikova, V. I.,Pivnitsky, K. K.
, p. 2489 - 2490 (2007/10/02)
Chiral synthons - (S)-5-hydroxymethyl-5(H)-furan-2-one and its t-butyldimethylsilyl ether - were synthsized from D-mannitol in 6-7 steps via 2-desoxy-D-ribonolactone derivatives.
THE CHEMISTRY OF O-SILYLATED KETENE ACETALS; DIASTEREOSELECTIVE ALDOL REACTION OF 2,3-O-ISOPROPYLIDENE-D (AND L)-GLYCERALDEHYDES LEADING TO 2-DEOXY-D (AND L)-RIBOSES
Kita, Yasuyuki,Yasuda, Hitoshi,Tamura, Osamu,Itoh, Fumio,Ke, Ya Yuan,Tamura, Yasumitsu
, p. 5777 - 5780 (2007/10/02)
Diastereoselective carbon-carbon bond forming reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes (D and L-2) with ketene silyl acetals (1a,b) occured in acetonitrile under mild conditions to give the corresponding anti-β-siloxyesters (D and L-3a) as major products, which could be converted through a few additional steps to 2-deoxy-D (and L)-riboses.
