98510-25-9

Upstream product

• 100-39-0 benzyl bromide 
• 98510-20-4 myo-inositol monoorthoformate 
• 98510-20-4 myo-Inositol orthoformate 
• 120268-33-9 4/6-O-benzyl-myo-inositol 1,3,5-monoorthoformate 
• 87-89-8 D-myo-inositol 
• 98510-22-6 (1R,3S,5S,6R,7S,8S,9S)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.1^3,7>decane-6,8-diol 

Downstream Products

• 98510-27-1 (8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decan-6-one 
• 135376-89-5 {[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester 
• 135346-05-3 [Fluoro-((1S,2R,3S,4R,5R,6S)-2,3,4,5,6-pentahydroxy-cyclohexyl)-methyl]-phosphonic acid 
• 135415-09-7 [Fluoro-((1R,2S,3R,4R,5S,6R)-2,3,4,5,6-pentahydroxy-cyclohexyl)-methyl]-phosphonic acid 
• 125288-06-4 4,6-di-O-benzyl-myo-inositol 2-dibenzylphosphate 
• 98510-27-1 (1S,5S,7R,8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decan-6-one 
• 149713-85-9 4,6-di-O-benzyl-myo-inositol 
• 28140-40-1 1,4,5,6-tetra-O-benzyl-myo-inositol 
• 214068-76-5 Octanoic acid (S)-2-[hydroxy-((1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrahydroxy-5-phosphonooxy-cyclohexyloxy)-phosphoryloxy]-1-octanoyloxymethyl-ethyl ester 
• 291527-81-6 Phosphoric acid dibenzyl ester (1S,2S,3R,4S,5R,6S)-2,3,4-tris-benzyloxy-5,6-dihydroxy-cyclohexyl ester 
• 638203-45-9 C₄₄H₅₀O₆ 
• 291527-89-4 Phosphoric acid dibenzyl ester (1S,2R,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4-dihydroxy-5-(4-methoxy-benzyloxy)-cyclohexyl ester 
• 291527-91-8 (-)-2,3,4,6-tetra-O-benzyl-myo-inositol-5-(dibenzyl phosphate) 
• 214068-76-5 Octanoic acid (S)-2-[hydroxy-((1R,2R,3R,4R,5S,6R)-2,3,4,6-tetrahydroxy-5-phosphonooxy-cyclohexyloxy)-phosphoryloxy]-1-octanoyloxymethyl-ethyl ester 

Relevant academic research and scientific papers

Phosphoric acid phaseomannite class compound and its preparation method and application (by machine translation)

The invention discloses a phaseomannite class phosphate compound, phosphoric acid phaseomannite class compound preparation method, and these phosphoric acid phaseomannite class compounds in the preparation of an anti-tumor drug. The use of non-small cell lung cancer cells to the compounds of this invention to inhibit the growth of tumor cells in active testing, that the compounds of this invention have high inhibition of tumor cell growth activity, some of the compound inhibiting activity even with cisplatin active quite, which indicates that the compounds of this invention have good cell penetrability and phosphorus esterase stability, can be used for the development of anti-tumor medicament. (by machine translation)

Synthesis and screening of novel inositol phosphonate derivatives for anticancer functions in vitro

Phosphonates have been frequently used as suitable isosteric and isoelectronic replacements for biologically important phosphates in the development of drugs or drug candidates because of their stability toward the action of phosphatases and other enzymes. In this paper, 12 mono-phosphonate inositol compounds were prepared with phosphonate instead of phosphate by two kinds of strategies, nucleophilic substitution and Arbuzov rearrangement, respectively. All compounds were evaluated in vitro for their activity against non-small cell lung cancer (NSCLC) cell line A549. Two compounds (3ac and 3bb) exhibited good antitumor activity at 10 μg/mL.

Desymmetrization of 4,6-diprotected myo-inositol

The asymmetric desymmetrization of 4,6-diprotected myo-inositol derivatives was achieved by using a bifunctional, readily available nucleophilic catalyst. The orthogonally protected products were obtained in 80-99% yield with 90-99% ee. Such structures serve as potential enantiopure building blocks for the synthesis of myo-inositol phosphates.

Synthesis and antitumor activity of inositol phosphotriester analogues

Inositol phosphates, as important second messengers of signal transduction, regulate many biological functions. However, cell penetration and phospholipase stability could be two main issues faced by inositol phosphate analogues used as lead compounds for drug discovery. Inositol phosphotriester analogues could be more beneficial to diffuse across plasma membrane. In this paper, we describe the design and synthesis of a series of inositol phosphotriester analogues based on phosphatidylinositol, along with the initial antitumor activity analysis. Several compounds exhibited good cytotoxic activity against human cancer cell lines A549, HepG2, MDA-MB-231 and HeLa, especially compound 33 was cytotoxic against all the four cancer cell lines with good IC50 values.

Thieme chemistry journal awardees - where are they now? synthesis of the marine glycolipid dioctadecanoyl discoside

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

Sulfonate protecting groups. Regioselective sulfonylation of myo-inositol orthoesters-improved synthesis of precursors of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 1,3,4,5,6-pentakisphosphate and related derivatives.

The regioselectivity of sulfonylation of myo-inositol orthoesters was controlled by the use of different bases to obtain the desired sulfonate. Monosulfonylation of myo-inositol orthoesters in the presence of one equivalent of sodium hydride or triethylamine resulted in the sulfonylation of the 4-hydroxyl group. The use of pyridine as a base for the same reaction resulted in sulfonylation of the 2-hydroxyl group. Disulfonylation of these orthoesters in the presence of excess sodium hydride yielded the 4,6-di-O-sulfonylated orthoesters. However, the use of triethylamine or pyridine instead of sodium hydride yielded the 2,4-di-O-sulfonylated orthoester. Sulfonylated derivatives of myo-inositol orthoesters were stable to conditions of O-alkylation but were cleaved using magnesium/methanol or sodium methoxide in methanol to regenerate the corresponding myo-inositol orthoester derivative. These new methods of protection-deprotection have been used: (i) for the efficient synthesis of enantiomers of 2,4-di-O-benzyl-myo-inositol, which are precursors for the synthesis of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate; (ii) for the preparation of 2-O-benzyl-myo-inositol which is a precursor for the preparation of myo-inositol 1,3,4,5,6-pentakisphosphate.

Racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate: A versatile intermediate for the preparation of myo-inositol phosphates

The versatility of racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5- orthoformate as an intermediate for the preparation of protected myo- inositol derivatives is demonstrated. Procedures described provide simple access to several protected myo-inositol derivatives which are intermediates for the preparation of myo-inositol phosphates and racemic ononitol.

Synthesis of an analogue of D,L-MYO-inositol-1,2-cyclic phosphate: Inhibition of phosphatidylinositol-specific phospholipase C

A fluorophosphonate analogue of myo-inositol-1,2-cyclic phosphate (cIP) has been synthesized: the specific, potent inhibition of a phosphatidyl inositol-specific phospholipase C (PI-PLC) by this compound is compared with inhibition by vanadate ion.

The Total Synthesis of myo-Inositol Phosphates via myo-Inositol Orthoformate

Novel selective alkylations of myo-inositol orthoformate (4) have been used to prepare a series of protected myo-inositol derivatives, (5a-e), (7), (10), (12), and (16).These intermediates have been used in efficient total syntheses of myo-inositol 2-phosphate, (9); myo-inositol 4-phosphate, (6); myo-inositol 1,3-bisphosphate, (18); and myo-inositol 1,3,4,5-tetrakisphosphate (14).This report represents the first total synthesis of the important natural metabolites (14) and (18) and significantly improved methods of preparation of (6) and (9).