6195-45-5Relevant academic research and scientific papers
A novel, mild palladium mediated deprotection of O-allyl and prop-1-enyl ethers
Mereyala, Hari Babu,Guntha, Sreenivasulu
, p. 6929 - 6930 (1993)
A mild method for the deprotection of diverse O-allyl (1a-5a) and prop-1-enyl ethers (1d-5d) of glycosides and inositol by use of PdCl2/CuCl/DMF-H2O/O2 is described.
Total Synthesis of Phospholipomannan of Candida albicans
Ali, Asif,Gannedi, Veeranjaneyulu,Singh, Parvinder Pal,Vishwakarma, Ram A.
, p. 7757 - 7771 (2020/07/25)
First, total synthesis of the cell surface phospholipomannan anchor [β-Manp-(1 → 2)-β-Manp]n-(1 → 2)-β-Manp-(1 → 2)-α-Manp-1 → P-(O → 6)-α-Manp-(1 → 2)-Inositol-1-P-(O → 1)-phytoceramide of Candida albicans is reported. The target phospholipomannan (PLM) anchor poses synthetic challenges such as the unusual kinetically controlled (1 → 2)-β-oligomannan domain, anomeric phosphodiester, and unique phytoceramide lipid tail linked to the glycan through a phosphate group. The synthesis of PLM anchor was accomplished using a convergent block synthetic approach using three main appropriately protected building blocks: (1 → 2)-β-tetramannan repeats, pseudodisaccharide, and phytoceramide-1-H-phosphonate. The most challenging (1 → 2)-β-tetramannan domain was synthesized in one pot using the preactivation method. The phytoceramide-1-H-phosphonate was synthesized through an enantioselective A3 three-component coupling reaction. Finally, the phytoceramide-1-H-phosphonate moiety was coupled with pseudodisaccharide followed by deacetylation to produce the acceptor, which on subsequent coupling with tetramannosyl-H-phosphonate provided the fully protected PLM anchor. Final deprotection was successfully achieved by Pearlman's hydrogenation.
ACETYLATED PRODRUGS FOR DELIVERY ACROSS THE BLOOD-BRAIN BARRIER
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, (2019/11/12)
The present disclosure relates to pharmaceutical compositions including a compound derived from a parent compound having a hydroxyl or amino moiety, wherein the hydroxyl in the parent compound is presented as an ester in the compound or the amino in the parent compound is presented as an amide in the compound, and their use to prevent or treat neurological disease.
Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues
Collet, Charlotte,Chrétien, Fran?oise,Chapleur, Yves,Lamandé-Langle, Sandrine
, p. 353 - 361 (2016/04/05)
Efficient routes were developed for the diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues. The key steps of the synthesis were the easy accessibility of different types of arms in term of con
The orientation of the β-hydroxyl group controls the diastereoselectivity during the hydride reduction and Grignard reaction of inososes
Jagdhane, Rajendra C.,Patil, Madhuri T.,Krishnaswamy, Shobhana,Shashidhar, Mysore S.
, p. 5144 - 5151 (2013/06/27)
A comparison of the results of the Grignard reaction and the hydride reduction of the carbonyl group of epi- and scyllo-inososes reveals that the extent of diastereoselectivity of these reactions is decided by the orientation of the β-hydroxyl group (or i
Intramolecular α-glucosaminidation: Synthesis of mycothiol
Ajayi, Kehinde,Thakur, Vinay V.,Lapo, Robert C.,Knapp, Spencer
supporting information; experimental part, p. 2630 - 2633 (2010/08/22)
A protected cyclitol aglycon was tethered to an (N-arylsulfonyl)glucosamine donor by a methylene linker; the exclusively α-selective intramolecular glycosyation reaction was then initiated by electrophilic activation of the thioglycoside donor portion. Further transformations of the glycosylation product to give the M. tuberculosis detoxifier mycothiol and its oxidized congener, the disulfide mycothione, are detailed.
Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation
Devaraj, Subramanian,Jagdhane, Rajendra C.,Shashidhar, Mysore S.
experimental part, p. 1159 - 1166 (2009/10/04)
O-Alkylation of myo-inositol derivatives containing more than one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results presented in this article as well as those available in the literature suggests that chelation of metal ions by inositol derivatives plays a significant role in the observed regioselectivity. Steric factors associated with the axial or equatorial disposition of the reacting hydroxyl groups do not contribute much to the outcome of these O-alkylation reactions. These results could serve as guidelines in planning synthetic strategies involving other carbohydrates and their derivatives.
COMPOUNDS AND COMPOSITIONS FOR THE DETECTION AND TREATMENT OF ALZHEIMER'S DISEASE AND RELATED DISORDERS
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, (2009/10/22)
One aspect of the present invention relates to compounds, compositions and methods for diagnosis and/or treatment of a subject suffering from an amyloidosis-associated pathological condition. In certain embodiments, the imaging and/or therapeutic agents of the instant invention may be administered to a subject for identification and/or treatment of amyloid deposits. A specific imaging method detects amyloid deposits by administering the imaging agent to the subject and detecting the spatial distribution of the agent. Differential accumulation of the agent is indicative of AD or an amyIoidosis-associated pathological condition and can be monitored by using a PET or SPECT camera.
Thieme chemistry journal awardees - where are they now? synthesis of the marine glycolipid dioctadecanoyl discoside
Florence, Gordon J.,Aslam, Tashfeen,Miller, Gavin J.,Milne, Gavin D. S.,Conway, Stuart J.
scheme or table, p. 3099 - 3102 (2010/03/02)
The first synthesis of the inositol-containing marine glycolipid dioctadecanoyl discoside is reported. The key glycosylation reaction proceeds with β-selectivity at reduced temperature. The separable anomers could be readily progressed to afford discoside
A synthesis of dioctanoyl phosphatidylinositol
Elliott, Thomas S.,Nemeth, Joseph,Swain, Simon A.,Conway, Stuart J.
experimental part, p. 2809 - 2813 (2010/03/30)
A synthesis of the naturally occurring enantiomer of phosphatidylinositol is reported. A resolution strategy, using camphor as a chiral auxiliary is employed to obtain the desired, enantiomerically pure, inositol derivative. Dioctanoyl lipid chains are appended to the molecule, which are shorter than the naturally occurring lipid chains, providing the molecule with enhanced water solubility.
