26276-99-3

Upstream product

• 76690-09-0 1⁽³⁾,2-di-O-(2-tetrahydropyranyl)3⁽¹⁾,4⁽⁶⁾,5,6⁽⁴⁾-tetra-O-benzyl-sn-myoinositol 
• 100-44-7 benzyl chloride 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 87-89-8 D-myo-inositol 
• 100-39-0 benzyl bromide 
• 64656-21-9 5,6-di-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol 
• 111392-21-3 5,6-di-O-acetyl-1,2,3,4-tetra-O-benzyl-myo-inositol 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 129662-34-6 (+/-)-1,2,4/3-2,3-Di-O-(2-methoxyethoxymethyl)cyclohex-5-ene-1,2,3,4-tetrol 
• 64656-21-9 C₄₀H₄₄O₆ 
• 6763-47-9 rac-1,2-O-cyclohexylidene-myo-inositol 
• 29847-13-0 (±)-1,4,5,6-tetra-O-benzyl-2,3-O-isopropylidene-myo-inositol 
• 23262-94-4 1⁽³⁾-O-(2-tetrahydropyranyl)-3⁽¹⁾,4⁽⁶⁾,5,6⁽⁴⁾-tetra-O-benzyl-sn-myoinositol 
• 23262-94-4 2-O-(2-tetrahydropyranyl)-1⁽³⁾,4⁽⁶⁾,5,6⁽⁴⁾-tetra-O-benzyl-sn-myoinositol 

Downstream Products

• 76690-09-0 1⁽³⁾,2-di-O-(2-tetrahydropyranyl)3⁽¹⁾,4⁽⁶⁾,5,6⁽⁴⁾-tetra-O-benzyl-sn-myoinositol 
• 23262-94-4 2-O-(2-tetrahydropyranyl)-1⁽³⁾,4⁽⁶⁾,5,6⁽⁴⁾-tetra-O-benzyl-sn-myoinositol 
• 23262-94-4 1⁽³⁾-O-(2-tetrahydropyranyl)-3⁽¹⁾,4⁽⁶⁾,5,6⁽⁴⁾-tetra-O-benzyl-sn-myoinositol 
• 112489-39-1 C₃₉H₄₂O₆ 
• 120144-52-7 (3aR,4R,5S,6S,7R,7aS)-4,5,6,7-Tetrakis-benzyloxy-2-methoxy-hexahydro-benzo[1,3,2]dioxaphosphole 
• 120144-51-6 Diisopropyl-phosphoramidous acid methyl ester (1R,2S,3R,4S,5R,6R)-2,3,4,5-tetrakis-benzyloxy-6-hydroxy-cyclohexyl ester 
• 120144-51-6 Diisopropyl-phosphoramidous acid methyl ester (1R,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis-benzyloxy-6-hydroxy-cyclohexyl ester 
• 154635-14-0 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1R,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis-benzyloxy-6-hydroxy-cyclohexyl ester 
• 154635-13-9 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2S,3R,4S,5R,6S)-2,3,4,5-tetrakis-benzyloxy-6-hydroxy-cyclohexyl ester 
• 6382-98-5 1,2,3,4,5,6-hexa-O-benzyl-myo-inositol 
• 6195-45-5 meso-1,3,4,5,6-penta-O-benzyl-myo-inositol 
• 23262-92-2 (+/-)-1-O-benzoyl-3,4,5,6-tetra-O-benzyl-myo-inositol 
• 135042-07-8 1-O-acetyl-3,4,5,6-tetra-O-benzyl-myo-inositol 
• 10583-42-3 (+/-)-1-O-allyl-3,4,5,6-tetrakis-O-benzyl myo-inositol 

Relevant academic research and scientific papers

Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: Does the reaction proceed through ‘axial rich’ conformation?

scyllo-Inositol derived 1,2-trans-diequatorial halohydrins can be efficiently converted to the corresponding epoxides in the presence of lithium hydride. The structure of one of the epoxides was determined by single crystal X-ray diffraction analysis. Thi

Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives

The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poo

Efficient regioselective protection of myo-inositol via facile protecting group migration

A cis-1,2-cyclohexanediol, 1,4,5,6-tetra-O-benzyl-myo-inositol, was selectively protected at the axial C2-hydroxyl via acid-mediated rearrangement of the corresponding 1,2-orthoacetate, or via the base-induced migration of a protecting group that had previously been easily installed with complete regioselectivity at the adjacent equatorial hydroxyl. Esters 4a-6a were synthesized in high yields (75-82%) while sulfonate 7a and silyl ether 8a were obtained in 85 and 31% yields, respectively. The migration of the esters induced by DBU results in equilibrium between regioisomers favouring the C2 protected isomer, but NaH induced migration of sulfonyl and silyl groups results in complete migration from equatorial to axial hydroxyl groups.

COMPOUNDS AND COMPOSITIONS FOR THE DETECTION AND TREATMENT OF ALZHEIMER'S DISEASE AND RELATED DISORDERS

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.

Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation

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.

INOSITOL-BASED MOLECULAR TRANSPORTERS AND PROCESSES FOR THE PREPARATION THEREOF

Inositol derivatives in accordance with the present invention are effective in significantly enhancing the transportation of various therapeutic molecules across a biological membrane, which may include the plasma membrane, nuclear membrane or blood-brain barrier.

Achievement of ring inversion of myo-inositol derivatives due to silyloxy/silyloxy repulsion enhanced by the trans-substituents on both sides

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

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.

Syntheses of penta-O-benzyl-myo-inositols, O-β-L-arabinosyl-(1 → 2)sn-myo-inositol, O-α-D-galactosyl-(1 → 3)-sn-myo-inositol, and O-α-D-galactosyl-(1 → 6)-O-α-D-galactosyl-(1 → 3)-sn-myo-inositol

Two-step conversions of myo-inositol into (±)-2,3,4,5,6- and 1,3,4,5,6-penta-O-benzyl-myo-inositols are described. Starting from these monohydroxy derivatives of myo-inositol, O-β-L-arabinopyranosyl-(1→2)-sn-myo-inositol from Japanese green tea, Camellia sinensis, and O-α-D-galactopyranosyl-(1→3)-sn-myo-inositol (galactinol) as well as its homolog, O-α-D-galactopyranosyl-(1→6(II))-galactinol, were synthesized by way of the in situ activating glycosylation procedure.

Practical synthesis of all inositol stereoisomers from myo-inositol

Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.