62445-01-6Relevant academic research and scientific papers
Synthesis of α-trinositol related analogues. Structure-activity (analgesic and anti-inflammatory) relationships
Ballereau,Rehnberg,Spiess,Gigg,Gigg,Schlewer
, p. 535 - 540 (1997)
α-Trinositol analogues, including methyl ethers, deoxy, oxa and aza derivatives were prepared. The parent compound possesses weak analgesic and anti-inflammatory properties. Removal of the non-phosphorylated hydroxyls generates a compound devoid of analgesic activity but which retains the anti-inflammatory property of the parent compound. The protection of these hydroxyls as methyl ethers lends to compounds which keep their anti-inflammatory activity, whereas the replacement of the cyclohexane carbone backbone by a tetrahydropyrane or a piperidine ring leads to compounds which increase the pain.
Molybdenum-catalyzed diastereoselective anti-dihydroxylation of secondary allylic alcohols
Su, Shixia,Wang, Chuan
supporting information, p. 2436 - 2440 (2019/03/29)
In this protocol, we report a Mo-catalyzed anti-dihydroxylation of secondary allylic alcohols, providing a general method for the preparation of 1,2,3-triols bearing up to three continuous stereocenters with excellent diastereocontrol. The mechanistic studies reveal that this dihydroxylation reaction consists of two steps and up to excellent diastereomeric ratios of the final triol products can be achieved due to the high level of both diastereocontrol in the initial epoxidation and regiocontrol in the following hydrolysis in situ.
Molybdenum-Catalyzed Hydroxyl-Directed Anti-Dihydroxylation of Allylic and Homoallylic Alcohols
Fan, Pei,Su, Shixia,Wang, Chuan
, p. 6820 - 6826 (2018/06/22)
A catalytic hydroxyl-directed anti-dihydroxylation of allylic and homoallylic alcohols has been developed. This operationally simple method was successfully applied to the direct anti-monodihydroxylation of allylic alcohols containing at least one distal olefinic unit. Under the catalysis of commercially available MoO2(acac)2, an array of hydroxylated dienes were successfully converted into various 1,2,3-triols using hydrogen peroxide as an environmentally benign oxidant under aerobic conditions, notably, in complete regioselectivities and in the most cases in diastereospecific pathway.
Conversion of racemic allylic hydroperoxides into corresponding chiral 1/2,3-triols by using catalytic OsO4 and chiral cinchona ligands in the absence of co-oxidant
G?ksu, Haydar,Gültekin, Mehmet Serdar
, p. 824 - 834 (2015/08/06)
For the first time, removal of oxygen atoms from allylic hydroperoxide functionality and reintroduction to the double bond was achieved using catalytic OsO4 and chiral cinchona alkaloid derivatives in an acetone-water mixture to give corresponding chiral 1/2,3-triol with an enantioselectivity up to 99% ee. The hydroperoxide group was used as both a co-oxidant and a source of hydroxyl groups. This protocol is thought to have potential to provide opportunities for chiral synthesis of 1/2,3-triols from corresponding allylic hydroperoxides in the absence of co-oxidant in one stage for the first time in the literature.
One-pot synthesis of 1,2/3-triols from the allylic hydroperoxides catalyzed by zeolite-confined osmium(0) nanoclusters
G?ksu, Haydar,Dalmizrak, Di?dem,Akbayrak, Serdar,Gültekin, Mehmet Serdar,?zkar, Saim,Metin, ?nder
, p. 142 - 147 (2013/08/23)
A facile, efficient and eco-friendly method for the one-pot synthesis of 1,2/3-triols from the allylic hydroperoxides were developed by using zeolite-confined osmium(0) nanoclusters as reusable catalyst and without using any co-oxidant (H2Osub
One-pot synthesis of 1,2,3-triols from allylic hydroperoxides and a catalytic amount of OsO4 in aqueous acetone
Alp, Cemalettin,Atmaca, Ufuk,?elik, Murat,Gültekin, Mehmet Serdar
experimental part, p. 2765 - 2768 (2010/02/28)
Allylic hydroperoxides were converted into the corresponding triols in the presence of a catalytic amount of OsO4. The present reaction involves regeneration of active osmium species by the hydroperoxide functionality and occurs in a diastereoselective manner to form triols in high yields. A plausible mechanism for the formation of 1,2,3-triols from allylic hydroperoxide is presented.
Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones
Hayashi, Yujiro,Yamaguchi, Junichiro,Sumiya, Tatsunobu,Hibino, Kazuhiro,Shoji, Mitsuru
, p. 5966 - 5973 (2007/10/03)
The direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones has been developed using nitrosobenzene as an oxygen source, affording α-anilinoxy-aldehydes and -ketones with excellent enantioselectivity. Reaction conditions have been optimized, and low temperature (-20 °C) was found to be a key for the successful α-aminoxylation of aldehydes, while slow addition of nitrosobenzene is essential for that of ketones. The scope of the reaction is presented.
THE SYNTHESIS OF CHIRAL ISOPROPYLIDENE DERIVATIVES OF 1,2,3-CYCLOHEXANETRIOLS BY ENZYMATIC DIFFERENTIATION
Dumortier, L.,Eycken, J. Van der,Vandewalle, M.
, p. 3201 - 3204 (2007/10/02)
2,3-O-Isopropylidene-1-cyclohexanol chiral building blocks have been prepared with high enantiomeric purities by enzymatic hydrolysis of their racemic acetates or n.butyrates.
ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS. EMPIRICAL RULE
Cha, J. K.,Christ, W. J.,Kishi, Y.
, p. 2247 - 2256 (2007/10/02)
An empirical formulation is presented to predict the stereochemistry of major osmylation products of allylic alcohols and their derivatives.
ON STEREOCHEMISTRY OF OSMIUM TETROXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS: EMPIRICAL RULE
Cha, J. K.,Christ, W. J.,Kishi, Y.
, p. 3943 - 3946 (2007/10/02)
An empirical formulation is presented to predict the stereochemistry of major osmylation products of allylic alcohols and their derivatives.
