28140-40-1Relevant articles and documents
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.
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.
Advances in analysis and synthesis of myo-inositol-derivatives through resolution by crystallisation
Wewers, Wolfgang,Gillandt, Hartmut,Traub, Henner Schmidt
, p. 1723 - 1728 (2007/10/03)
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
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.
Stable axial-rich chair conformer of myo-inositol derivatives due to introduction of two adjacent bulky silyl protections
Yamada, Hidetoshi,Okajima, Kotaro,Imagawa, Hiroshi,Mukae, Tatsuya,Kawamura, Yoshiaki,Nishizawa, Mugio
, p. 3157 - 3160 (2007/10/03)
The ring-conformational change of myo-inositol derivatives by introducing two tert-butyldimethylsilyl, triisopropylsilyl, or tert-butyldiphenylsilyl groups into the 1,2-trans hydroxy groups - 3,4- and 4,5-positions - were investigated. The cyclohexane cores of the 4,5-bis-O-silylated derivatives with tert-butyldiphenylsilyl or triisopropylsilyl groups were present in the axial-rich chair form.
L-chiro-inositol derivatives from myo-inositol. Building blocks for inositolphosphoglycans
Cid, M. Belén,Alfonso, Francisco,Martín-Lomas, Manuel
, p. 1370 - 1372 (2007/10/03)
A straightforward synthesis of L-chiro-inositol, deoxy L-chiro-inositol derivatives and L-chiro-inositol building blocks for the preparation of inositolphosphoglycans, is reported from myoinositol. Glycosylation with 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-g
Total synthesis of spicamycin
Suzuki, Tamotsu,Suzuki, Sayaka T.,Yamada, Iwao,Koashi, Yoshiaki,Yamada, Kazue,Chida, Noritaka
, p. 2874 - 2880 (2007/10/03)
The first total synthesis of one of the spicamycin congeners, SPM VIII (3), is described. A preliminary model study for construction of the characteristic N-glycoside linkage in spicamycin using tetra-O-benzyl-β-D-mannopyranosylamine (13) and halopurines 5 revealed that Pd-catalyzed conditions successfully provided the coupling products 14 and 15 in good yields. It was also shown that thermal anomerization of the N-glycosides easily occurred, which resulted in the predominant formation of the β-anomer as the thermodynamically favored compound, and the activation energy of anomerization of 15 was estimated to be ca. 30 kcal/mol. The novel aminoheptose unit of spicamycin 6 was prepared stereoselectively by carbon elongation of an acyclic aldehyde, prepared by ring cleavage reaction of a highly functionalized cyclohexane derived from naturally abundant myo-inositol. The Pd-catalyzed coupling reaction of the β-heptopyranosylamine 6 with protected 6-chloropurine 5d, followed by deprotection, provided spicamycin amino nucleoside 2, whose condensation with dodecanoylglycine completed the total synthesis of 3. This study confirmed the proposed unique structure of a novel nucleoside antibiotic.
Synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] and its diastereoisomers
Gaffney, Piers R.J.,Reese, Colin B.
, p. 192 - 205 (2007/10/03)
The chemical synthesis of naturally occurring phosphatidylinositol 3,4,5-triphosphate [PtdIns(3,4,5)P3] and its diastereoisomers was discussed. In the first stage, the preparation of the required enantiomeric 1,2-di-O-acylglycerol derivatives was done. The second stage involved the preparation of suitably protected enantiomeric myo-inositol 1-phosphates. The glycerol and inositol building blocks were coupled together and the 3-, 4- and 5-hydroxy functions of the inositol residues in the coupled products were phosphorylated. Finally, the protecting groups were removed to give PtdIns(3,4,5)P3 and its diastereoisomers.
Convenient synthesis of 2-deoxy-scyllo-inosose and 2-deoxy-scyllo-inosamine: Two key intermediates on the biosynthetic pathway to aminoglycoside antibiotics
Yu, Jinquan,Spencer, Jonathan B
, p. 4219 - 4221 (2007/10/03)
2-Deoxy-scyllo-inosose 1 and 2-deoxy-scyllo-inosamine 2 are two of the key intermediates on the biosynthetic pathway to 2-deoxystreptamine-containing aminoglycoside antibiotics. Convenient syntheses of 1, 2 and tritium-labelled 2 via stereoselective deoxy
Preparation of L-α-phosphatidyl-D-myo-inositol 3-phosphate (3-PIP) and 3,5-biphosphate (3,5-PIP2)
Falck,Krishna, U. Murali,Capdevila, Jorge H.
, p. 1711 - 1713 (2007/10/03)
Practical, asymmetric total syntheses of the title phospholipids from a readily available myo-inositol derivative as well as short chain and cross-linkable aminoether analogues are described. (C) 2000 Elsevier Science Ltd. All rights reserved.
