24558-77-8Relevant academic research and scientific papers
Advances in analysis and synthesis of myo-inositol-derivatives through resolution by crystallisation
Wewers, Wolfgang,Gillandt, Hartmut,Traub, Henner Schmidt
, p. 1723 - 1728 (2005)
A simple method for the preparation of both enantiomers of tetra-O-benzyl-myo-inositol is presented. This method is based on the resolution of stereoisomers by crystallisation. Starting with the known synthesis of four diastereomers using d-camphor dimeth
Enzymatic resolution of the sterically hindered myo-inositol derivative
Ling,Ozaki
, p. 1200 - 1205 (1995)
A modification of the enzymatic resolution has been developed for the resolution of the sterically hindered myo-inositol derivative. In this method, a side chain, which contains a terminal hydroxyl group on it, was introduced to a chiral hydroxyl group, and the terminal hydroxyl group on side chain was used for resolution. Enzymes could recognize the asymmetric center through the distal terminal hydroxyl group. Racemic 3,4,5,6-O-tetrabenzyl-myo-inositol was resolved by this method.
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.
Introducing Oxo-Phenylacetyl (OPAc) as a Protecting Group for Carbohydrates
Kumar, Atul,Gannedi, Veeranjaneyulu,Rather, Suhail A.,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
, p. 4131 - 4138 (2019/04/30)
A series of oxo-phenylacetyl (OPAc)-protected saccharides, with divergent base sensitivity profiles against benzoyl (Bz) and acetyl (Ac) were synthesized, and KHSO5/AcCl in methanol was identified as an easy, mild, selective, and efficient deprotecting reagent for their removal in the perspective of carbohydrate synthesis. Timely monitoring of AcCl reagent was supportive in both sequential and simultaneous deprotecting of OPAc, Bz, and Ac. The salient feature of our method is the orthogonal stability against different groups, its ease to generate different valuable acceptors using designed monosaccharides, and use of OPAc as a glycosyl donar.
N-heterocyclic carbene-catalyzed benzoin strategy for divergent synthesis of cyclitol derivatives from alditols
Kang, Bubwoong,Sutou, Toshiaki,Wang, Yinli,Kuwano, Satoru,Yamaoka, Yousuke,Takasu, Kiyosei,Yamada, Ken-Ichi
, p. 131 - 147 (2015/01/30)
A divergent synthesis of cyclitol derivatives has been developed utilizing an N-heterocyclic carbene-catalyzed benzoin-type cyclization of C2-symmetrical dialdoses. The resulting inososes are versatile intermediates, which are readily converted
The myo-1,2-diaminocyclitol scaffold defines potent glucocerebrosidase activators and promising pharmacological chaperones for gaucher disease
Trapero, Ana,Llebaria, Amadeu
supporting information; experimental part, p. 614 - 619 (2011/10/08)
A series of cyclitol derivatives with myo-configuration are β-glucocerebrosidase (GCase) inhibitors and show excellent characteristics for the development of pharmacological chaperones for enzyme deficiency in Gaucher disease (GD). The most potent inhibit
SYNTHETIC ANALOGUES OF PHOSPHATIDYL-MYO-INOSITOL MANNOSIDES WITH AN INHIBITORY ACTIVITY OF THE INFLAMMATORY RESPONSE
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Page/Page column 9, (2011/10/04)
The present invention relates to novel synthetic analogues of phosphatidyl-myo-inositol mannosides (hereinafter referred to as PIMs) of general formula (I): or a pharmaceutically acceptable salt thereof, to the method for preparing same and to the use thereof in the prevention or treatment of a disease associated with the overexpression of cytokines or of chemokines, in particular of TNF and/or of IL-12. The invention also relates to a pharmaceutical composition comprising at least one synthetic derivative of PIM.
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.
Enantio- and diastereodivergent synthetic route to multifarious cyclitols from D-xylose via ring-closing metathesis
Luchetti, Giovanni,Ding, Kejia,D'Alarcao, Marc,Kornienko, Alexander
experimental part, p. 3142 - 3147 (2009/04/06)
Short stereoselective syntheses of various cyclitols, including the derivatives of conduritol B, conduritol F, myo-inositol, and chiro-inositol have been accomplished. The key steps in the syntheses are a ring-closing metathesis process and a diastereodiv
Achievement of ring inversion of myo-inositol derivatives due to silyloxy/silyloxy repulsion enhanced by the trans-substituents on both sides
Okajima, Kotaro,Mukae, Tatsuya,Imagawa, Hiroshi,Kawamura, Yoshiaki,Nishizawa, Mugio,Yamada, Hidetoshi
, p. 3497 - 3506 (2007/10/03)
The introduction of quite bulky trialkyl or diarylalkylsilyl groups into vicinal trans-hydroxy groups induced a conformational flip of certain multifunctionalized cyclohexane rings from the usual chair form possessing more equatorial substituents (equatorial-rich chair form) into another chair-form that has more axial substituents (axial-rich chair form). This realization was experimentally revealed by the conformational study of the synthetic myo-inositol derivatives possessing two tert-butyldimethylsilyl (TBS), two triisopropylsilyl (TIPS), or two tert-butyldiphenylsilyl (TBDPS) groups on an adjacent trans-diol. Among them, the cyclohexane rings of the 4,5-bis-O-TIPS-myo-inositol, 4,5-bis-O-TBDPS-myo-inositol, and 1,2,3,6-tetra-O-benzyl-4,5-bis-O-TBDPS-myo-inositol were in the axial-rich chair form. Comparison of the ring conformations also revealed that the order of the repulsion was OTBDPS/OTBDPS>OTIPS/OTIPS>OTBS/OTBS, and the silyloxy/silyloxy repulsion was enhanced when the two silyloxy groups were placed in the center of the contiguous four equatorial substituents.
