1.2.4- Triols

The application of this procedure to (racemic) hydroxy-substituted allylmolybdenum complexes, such as 3, yields diastereomerically pure 1,3-diols (e.g. ) or 1,3,5-triols (e.g. ) via the corresponding 1,3-dioxanes6 4 ... 

For further applications of this Noyori ketalization compare, e.g. Refs. [6-15]. Interesting also are the reactions of silylated 1,3-diols and 1,3,5-triols with l-... 

Diols and polyols can participate in equilibria with boric acid in aqueous solution. The stability of polyolborates is determined by the number of OH groups in cis positions. Complexes with polyols are more stable than with diols, and 1,2-diol complexes are more stable than their 1,3-diol counterparts (Table 10) since the resulting five-membered chelate ring is unstrained.75120 In the case of 1,3,5-triols stable cage-like structures (5) and (6) are favored. Open-chain or five-membered cyclic polyols form more stable chelate complexes than their six-membered counterparts.120 Thus, chelates from alditols and ketohexoses are more stable than the corresponding aldose chelates (Table 10). Many polyols allow quantitative titrimetric determination of boric acid. Of these, mannitol remains the most widely used reagent on the basis of availability, cost and ease of handling.75... 

Tandem intramolecular silylformylation-allylation reaction of diallylhydrosilyl ethers derived from homoallyl alcohols is convenient for rapid, stereoselective synthesis of 1,3,5-triols convertible to more oxygen-functionalized compounds (Scheme 12).142,142a,142b 143 [ he second uncatalyzed allylation step would be facilitated by the formation of a strained silacycle intermediate, which has enough Lewis acidity to activate the formyl group. A similar tandem reaction via alkyne silylformylation has been reported.144... 

Oxidative cyclisation of p-methoxybenzyl ethers can be used to accomplish de-svmmetrisation of 1,3,5-triols with good to excellent regioselectivity [Scheme... 

A highly useful twofold reaction of silyl dithioacetals with epoxides was described by Tietze and coworkers (Scheme 2.107) [249]. Treatment of 2.2equiv. of enan-tiopure epoxides 2-463 with lithiated silyldithiane 2-458b in the presence of a crown ether led to 2-467 after aqueous work-up. It can be assumed that by attack of the lithium compound 2-462 at the sterically less-hindered side of the epoxide 2-463, the alkoxide 2-464 is formed which in a subsequent Brook rearrangement produces the lithium dithioacetal 2-465. This reacts again with an epoxide to give 2-466 and furthermore 2-467. Treatment with NaF then leads to the diol 2-468 which can be converted into the dihydroxy ketones 2-469 and the corresponding 1,3,5-triols, respectively. 

SYNS BENZENE-s-TRIOL BENZENE-1,3,5-TRIOL 1,3,5-BENZENETRIOL 3,5-DIHYDROXYPHENOL DILOSPAN S 5-OXYRESORCINOL PHLORO-GLUCIN s-TRIHYDROXYBENZENE sym-TRI-HYDROXYBENZENE 1,3,5-TRIHYDROXYBENZENE 1,3,5-TRIHYDROXYCYCLOHEXATRIENE... 

Benzene-1.3,5-triol (phloroglucinol) undergoes reaction with benzofuroxan in methanol with a primary amine as base to give phenazine-l,3-diol 5,10-dioxide.Phenazine-2,3-diol 5,10-dioxides are also synthesized by the reaction of benzene-1,2,4-triol with 6-substituted benzo-furoxans. ... 

Isolated from a Bahamian collection of L. majuscula, caylobolide (73) is a unique 36-membered macrolactone that shows cytotoxicity to human colon cancer cell line HCT-166. Caylobolide contains a 1,3,5-triol and a repeating 1,5-diol within the macrocycle. The 1,5-diol had not been reported before the isolation of caylobolide and points to a unique biosynthetic pathway. Additionally, this compound is interesting because of its being atypical of the metabolites usually isolated from cyanobacteria. The 1,5-diol repeat is likely produced from PKS modules that catalyze full reduction of the /1-ketone alternating with those that simply reduce the /1-ketone to an... 

ESTANO (Spanish) (7440-31-5) Finely divided material is combustible and forms explosive mixture with air. Contact with moisture in air forms tin dioxide. Violent reaction with strong acids, strong oxidizers, ammonium perchlorate, ammonium nitrate, bis-o-azido benzoyl peroxide, bromates, bromine, bromine pentafluoride, bromine trifluoride, bromine azide, cadmium, carbon tetrachloride, chlorine, chlorine monofluoride, chlorine nitrate, chlorine pentafluoride, chlorites, copper(II) nitrate, fluorine, hydriodic acid, dimethylarsinic acid, ni-trosyl fluoride, oxygen difluoride, perchlorates, perchloroethylene, potassium dioxide, phosphorus pentoxide, sulfur, sulfur dichloride. Reacts with alkalis, forming flammable hydrogen gas. Incompatible with arsenic compounds, azochloramide, benzene diazonium-4-sulfonate, benzyl chloride, chloric acid, cobalt chloride, copper oxide, 3,3 -dichloro-4,4 -diamin-odiphenylmethane, hexafluorobenzene, hydrazinium nitrate, glicidol, iodine heptafluoride, iodine monochloride, iodine pentafluoride, lead monoxide, mercuric oxide, nitryl fluoride, peroxyformic acid, phosphorus, phosphorus trichloride, tellurium, turpentine, sodium acetylide, sodium peroxide, titanium dioxide. Contact with acetaldehyde may cause polymerization. May form explosive compounds with hexachloroethane, pentachloroethane, picric acid, potassium iodate, potassium peroxide, 2,4,6-trinitrobenzene-1,3,5-triol. 

This methodology was utilized in conjunction with peroxide reduction as a ster-eocontrolled pathway to allylic 1,3-diols [98], The single-electron reductant SmF was found to be especially effective for this purpose [100]. An application of this chemistry to the synthesis of a naturally occurring 1,3,5-triol has been reported [98, 100]. 

Beilstein Handbook Reference) AI3-08848 Benzene, trihydroxy Benzene, 1,3,5-trihydroxy- Benzene-1,3,5-triol Benzene-s-triol 1,3,5-Benzenetriol BRN 1341907 CCRIS 4147... 

There are few known cases of azo coupling with classical aromatic coupling components, e.g., diazomethane, ethyl diazoacetate, and diazoketones with benzene-1,3,5-triol (Severin, 1958) and dicyanodiazomethane with A,A-dimethylaniline (Ciganek, 1965 a). 

Benzene-1,3,5-triol 1,3,5-Benzenetriol Benzene-s-triol. See 1,3,5-Trihydroxybenzene Benzene, 1,3,5-tris (1-methylethyl). See 1,3,5-T ri isopropyl benzene Benzenol. See Phenol Benzenyl chloride. See Benzotrichloride Benzenyl fluoride. See Benzotrifluoride Benzenyl trichloride. See Benzotrichloride Benzethonium Chioride USP. See Benzethonium chloride Benzethonium chloride CAS 121-54-0 EINECS/ELINCS 204-479-9 Synonyms Benzyidimethyl (2-(2-(p-(1,1,3,3-tetramethylbutyl) phenoxy) ethoxy) ethyl) ammonium chloride ... 

CAS 108-73-6 6099-90-7 (dihydrate) EINECS/ELINCS 203-611-2 Synonyms Benzene-1,3,5-triol 1,3,5-Benzenetriol Benzene-s-triol 3,5-... 

Silylformylation is a powerful synthetic tool for the synthesis of substituted-formylvinylsilanes. In 2001, the des3nnmetrization of dimethylsiloxyalkadiynes 80 to afford 81 as well as a novel sequential double silylformylation affording an unsaturated cyclooxasilanes (82) was reported. The product afforded by single desymmetrization reaction can subsequently be converted to 1,3,5-triols by way of Tamao oxidation, with subsequent reduction of the resultant keto-aldehyde. Additionally, it was found that use of phenyldimefliylhydrosilane decreased the reaction time, whereas use of bulkier hydrosilanes, e.g., /-butyldimethylsilane required both increased time and temperature. ... 

It has also been proposed to use 1,3-diols, 1,3,5-triols, amino-1,3-diols, or hydroxyamide derivatives as anti-curl agents in the ink in order to suppress curling (56). 

Tietze, L. F., Geissler, H., Gewert, J. A., Jakobi U. (1994). Tandem-bisalkylation of 2-trialkylsilyl-l,3-dithiane a new sequential transformation for the synthesis of Cj-symmetrical enantiopure 1,5-diols and f), 3 -dihydroxyketones as well as of enantiopure 1,3,5-triols. Synlett, 511-512. 

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