130669-76-0

Usage

Uses

Used in Organic Synthesis:
(3AS)-3A 4 5 7A-TETRAHYDRO-2 2-DIMETHYL& is used as a chemical intermediate for [application reason] in the field of organic synthesis.
Used as a Reagent in Chemical Reactions:
In the chemical industry, (3AS)-3A 4 5 7A-TETRAHYDRO-2 2-DIMETHYL& is used as a reagent for [application reason] in various chemical reactions.
Note: The exact application reasons for organic synthesis and as a reagent in chemical reactions are not provided in the materials. They have been left as placeholders to be filled in with specific details once the compound's properties and uses are better understood through further research.

InChI:InChI=1/C9H14O4/c1-9(2)12-6-4-3-5(10)7(11)8(6)13-9/h3-8,10-11H,1-2H3/t5-,6-,7-,8-/m1/s1

Upstream product

• 137501-12-3 (3aS,4R,5R,7aS)-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole-4,5-diol 
• 165611-18-7 (3aS,4R,5R,7aS)-7-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol 
• 906653-85-8 (3aS,4R,5S,7aS)-2,2 dimethyl-6,7-dibromo-4,5-dihydroxybenzo[1,3]dioxole 
• 154013-21-5 (3aR,5aS,8aS,8bR)-4-bromo-2,2,7,7-tetramethyl-3a,5a,8a,8b-tetrahydrobenzo<1,2-d>;<3,4-d'>bis<1,3>dioxole 
• 108-86-1 bromobenzene 
• 130669-75-9 (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 
• 583-53-9 2,3-dibromobenzene 
• 906653-84-7 (3aS,7aS)-2,2-dimethyl-4,5-dibromo-4,6-benzo[1,3]dioxole 
• 906653-83-6 (1S,2S)-3,4-dibromo-cyclohexa-3,5-diene-1,2-diol 

Downstream Products

• 137567-79-4 (1R,2R,3R,4R)-5-cyclohexene-1,2,3,4-tetrol 
• 10284-63-6 pinitol 
• 643-10-7 allo-inositol 

Relevant academic research and scientific papers

Arene cis-dihydrodiols: Useful precursors for the preparation of analogues of the anti-tumour agent, 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC)

The synthesis of 6-epi-COTC, a diastereoisomer of Streptomyces metabolite 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC), is described. The anti-cancer activities of the novel analogue, in racemic and enantiomerically pure forms, a

Use of Electrochemical Methods as an Alternative to Tin Reagents for the Reduction of Vinyl Halides in Inositol Synthons

Several vinyl halides previously used in inositol syntheses were subjected to electrochemical reduction. The unreactivity of allylic alcohols or allylic ethers at the applied potentials allowed the selective reduction of vinyl halides to olefins. Electrochemical methods provide for selective reduction of vinyl iodides over vinyl bromides, with better yields than analogous tin methodology. Cinnamyl ethers were reductively cleaved at -3.2 V (vs Ag/AgNO3) in the presence of alkyl allyl ethers to provide selective deprotection. The electrochemical reduction of vinyl halides in the presence of a vinyloxirane or vinylaziridine is accompanied by the solvolysis of the strained rings. Yields and conditions are reported and compared to those from standard tin-induced dehalogenation.

A chemoenzymatic route to chiral siloxanes

An approach employing two enzymes—toluene dioxygenase and immobilized lipase B from Candida antarctica (N435)—was explored as a potential biocatalytic method for the coupling of chiral diols with siloxane species. Analysis of reaction mixtures using1H NMR spectroscopy suggested that up to 66% consumption of the siloxane starting materials had occurred. Oligomeric species were observed and chiral products from the coupling of a cyclic diol with a siloxane molecule were isolated and characterized by MALDI-ToF MS and GPC. Immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus were also explored as potential catalysts for the coupling reactions, however, their use only returned starting material.

Toluene dioxygenase-mediated oxidation of dibromobenzenes. Absolute stereochemistry of new metabolites and synthesis of (-)-conduritol E

Dibromobenzenes (o-, m-, and p-isomers) were converted to the corresponding cis-cyclohexadiene diols by whole-cell fermentation with Escherichia coli JM 109 (pDTG601A), an organism over-expressing the enzyme toluene dioxygenase (TDO). Absolute stereochemi

Synthesis of chiral ADMET polymers containing repeating D-chiro-inositol units derived from a biocatalytically prepared diene diol

Several chiral hydroxylated polymers have been prepared, via ADMET techniques, from the diene diol derived from bromobenzene, obtained by means of whole-cell fermentation with Escherichia coli (JM109 pDTG601).

Selective electrochemical reduction of cinnamyl ethers in the presence of other allylic C-O bonds

Several conduritol derivatives protected as allyl and cinnamyl ethers were subjected to electrochemical reduction at a mercury cathode, resulting in selective removal of the cinnamyl group.

Enantiopure arene dioxides: Chemoenzymatic synthesis and application in the production of trans-3,4-dihydrodiols

Enantiopure syn- and anti-arene dioxides are synthesised from cis-dihydrodiol metabolites; anti-benzene dioxides are reduced to enantiopure trans-3,4-dihydrodiols while synbenzene dioxides racemise thermally via 1,4-dioxocins.

Chemoenzymatic enantiodivergent synthesis of 1,2-dideoxy-2-amino-1- fluoro-allo-inositol

Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (-)-9 were synthesized from bromocyclohexadiene cis-diol 1 obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through S(N)2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fluoride dihydrofluoride (TBPF-DF).

A practical multigram-scale synthesis of allo-inositol

Allo-Inositol was prepared on a multigram scale starting with bromobenzene in seven steps by three different cis-dihydroxylations (enzymatic, OsO4 and RuO4 catalyzed) employed in tandem.