45775-30-2

Basic information

• Product Name: Cyclohexane-1α,2α,4β,5β-tetrol
• Synonyms: 1α,2α,4β,5β-Cyclohexanetetrol;Cyclohexane-1α,2α,4β,5β-tetrol;[1S,2S,4S,5S,(+)]-1,2,4,5-Cyclohexanetetrol
• CAS NO: 45775-30-2
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.15708
• Mol File: 45775-30-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclohexane-1α,2α,4β,5β-tetrol(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexane-1α,2α,4β,5β-tetrol(45775-30-2)
• EPA Substance Registry System: Cyclohexane-1α,2α,4β,5β-tetrol(45775-30-2)

Safety Data

• Hazardous Substances Data: 45775-30-2(Hazardous Substances Data)

Upstream product

• 1165952-92-0 cyclohexa-1,4-diene 
• 143615-77-4 cyclohexane-r-1,c-2,t-4,t-5-tetrayl tetraactetate 
• 285-52-9 1,4-cyclohexadiene diepoxide 
• 97949-68-3 (1S,3R,4S,6R)-7-Oxa-bicyclo[4.1.0]heptane-3,4-diol 
• 6261-00-3 (+/-)-1r,2t,4c,5t-tetrakis-benzoyloxy-cyclohexane 
• 406682-04-0 cis-cyclohex-4-ene-1,2-diol 

Downstream Products

• 6261-00-3 (+/-)-1r,2t,4c,5t-tetrakis-benzoyloxy-cyclohexane 
• 120-12-7 anthracene 
• 6261-46-7 (+/-)-1r,2t,4c,5t-tetraacetoxy-cyclohexane 
• 143615-77-4 cyclohexane-r-1,c-2,t-4,t-5-tetrayl tetraactetate 

Relevant articles and documents

Benzannulation via ruthenium-catalyzed diol-diene [4+2] cycloaddition: One- and two-directional syntheses of fluoranthenes and acenes

A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol-diene [4+2] cycloaddition delivers cyclohex-1-ene-4,5-diols, which are subject to aromatization upon dehydration or Nicholas diol deoxydehydration. Employing diol and tetraol reactants, benzannulation can be conducted efficiently in one- and two-directional modes, respectively, as illustrated in the construction of substituted fluoranthenes and acenes.

Synthesis of diols using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate)

1,2- and 1,3-Bis(trifluoroacetoxy) alcohols are easily obtained from the one-pot reaction of alkenes with phenyliodine(III) bis(trifluoroacetate) (PIFA) in the absence of any additive or catalyst. The products were converted into the corresponding diols by ammonolysis. The use of bicyclic alkenes has shown that rearranged 1,3-diacetoxy alcohols are mostly formed as the major products.

Scope of the directed dihydroxylation: Application to cyclic homoallylic alcohols and trihaloacetamides

The synthesis and directed dihydroxylation of a range of cyclic alkenes was investigated. Both homoallylic alcohols and homoallylic trihaloacetamides were found to be efficient directing groups, giving rise to good to excellent levels of remote asymmetric induction with OsO4-TMEDA. Interestingly, in all cases examined, trifluoroacetamides were found to be superior to trichloroacetamides as directing groups and an argument is presented which rationalises this observation.

On the stereoselectivity in bisdihydroxylation of 1,5-cyclooctadiene with osmium tetroxide

In the bisdihydroxylation of 1,5-cyclooctadiene with OsO4, use of a stoichiometric amount of OsO4 yielded a 1:1 mixture of syn- and anti-isomers, while use of a catalytic amount of OsO4 gave only syn-(1R*,2S*,5R*,6S*)-cyclooctane-1,2,5,6-tetrol. This syn-selectivity was attributed to the favorable formation of an intramolecular osmium(VI) bisglycolate ester in the catalytic reaction.

Dihydroxylation of polyenes using Narasaka's modification of the upjohn procedure

Dihydroxylation of a variety of commercially available polyenes has been investigated using phenylboronic acid, .ZV-methylmorpholine Af-oxide (NMO), and osmium tetroxide in anhydrous solvent. The diastereoselectivity of multiple oxidation steps is in some cases affected by the in situ protection of the intermediate ene-diols as phenyboronic esters, affording polyols not available from the standard Upjohn dihydroxylation procedure. A convenient oxidative deprotection of the phenylboronic esters is also described.

One-pot synthesis from 1,4-cyclohexadiene of (±)-1,4/2,5-cyclohexanetetrol, a naturally occurring cyclitol derivative

SeO2-catalyzed direct hydroxylation of 1,4-cyclohexadiene with two molar equivalents of 30% H2O2 afforded (±)-1,4/2,5-cyclohexanetetrol, a naturally occurring cyclitol derivative, as the sole product in a good yield (88%).

Catalytic One-Pot Osmylation of Cyclohexadienes: Stereochemical and Conformational Studies of the Resulting Polyols

Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H2O in the presence of the co-oxidant N-methylmorpholine N-oxide (NMO).The formation of polyols occurred stereospecifically with cyclohexadienes 3, 7, and 11a, leading thereby to tetrols 5a, and 9a and to allo-inositol (14a), respectively.To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (neo), and 20a (chiro).High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.