174966-55-3

Upstream product

• 130021-74-8 (1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol 
• 98-88-4 benzoyl chloride 
• 203317-81-1 (1R,2R,3S)-5-(benzoyloxymethyl)-1,2-O-cyclohexylidene-4-cyclohexene-1,2,3-triol 
• 131221-89-1 (1R,2R,3S)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol 
• 174966-54-2 (1R,2R,3S)-3-O-tert-butyldimethylsilyl-5-benzoyloxymethyl-1,2-O-cyclohexylidene-4-cyclohexen-1,2,3-triol 

Downstream Products

• 175979-28-9 (1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 
• 203457-70-9 Benzoic acid (1S,2S,3R,6S)-2-acetoxy-3-hydroxy-7-oxa-bicyclo[4.1.0]hept-4-en-1-ylmethyl ester 
• 203457-68-5 Benzoic acid (1R,2S,3R,6R)-2-acetoxy-3-hydroxy-7-oxa-bicyclo[4.1.0]hept-4-en-1-ylmethyl ester 
• 176198-54-2 Benzoic acid (1R,4R,7S,8S)-7-acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester 
• 175979-31-4 Benzoic acid (1S,4S,7S,8S)-7-acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester 
• 175979-33-6 Benzoic acid (1R,2R,4R,5S,6R,7S)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester 
• 176198-56-4 Benzoic acid (1S,2S,4S,5S,6R,7R)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester 
• 176198-55-3 Benzoic acid (1R,4R,7S,8S)-7-acetoxy-8-hydroxy-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester 
• 175979-32-5 Benzoic acid (1S,4S,7S,8S)-7-acetoxy-8-hydroxy-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester 
• 175979-34-7 4-benzoyloxymethyl-3,8-dioxatricyclo[5.1.0.0^2,4]octane-5,6-diol 5-acetate 
• 176198-57-5 Benzoic acid (1S,2S,4S,5S,6R,7S)-5-acetoxy-6-hydroxy-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester 
• 203317-83-3 (1R,2R,3S,4R)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidene-5-cyclohexene-1,2,3,4-tetrol 
• 175979-29-0 Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester 
• 175979-30-3 Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester 

Relevant academic research and scientific papers

Enantiospecific syntheses of (+)-crotepoxide, (+)-boesenoxide, (+)-β- senepoxide, (+)-pipoxide acetate, (-)-iso-crotepoxide, (-)-senepoxide, and (- )-tingtanoxide from (-)-quinic acid

A convenient strategy that is ideally suited for the Construction of all the naturally occurring cyclohexane diepoxides and cyclohexene epoxides is described. The key intermediate 12, a 1,3-cyclohexadiene, has been prepared from (-)-quinic acid in 11 steps with 18% overall yield: Singlet oxygen photooxygenation of the 1,3-cyclohexadiene followed by rearrangement of the resultant endoperoxides with either cobalt-meso-tetraphenylporphyrin or trimethyl phosphite afforded enantiopure (+)-crotepoxide, (+)-boesenoxide, and (-)-iso-crotepoxide or (-)-senepoxide, (+)-β-senepoxide, (+)-pipoxide acetate, and (-)-tingtanoxide, respectively.

Rhutenium-Catalyzed cis-Dihydroxylation of Alkenes: Scope and Limitations

Oxidative ruthenium catalysis (0.07 molequiv RuCl3*(H2O)3, 1.5 molequiv NaIO4, EtOAc/CH3CN/H2O 3:3:1), beyond the usual C-C bond cleavage to give dicarbonyls, have been shown to syn-dihydroxylate a wide range of alkenes (except for strained bicyclic alkenes, sterically hindered trisubstituted alkenes, and most tetrasubstituted alkenes) to give vicinal diols rapidly (within minutes) and efficiently.The minor products are the usual oxidative fission products, namely, ketones and aldehydes or carboxylic acids, and sometimes ketols.Longer reaction times lower the yields of most diols, probably owing to oxidative glycol cleavage.Reactions with substrates containing one or more electron-withdrawing groups in conjugation with or adjacent to the alkene moiety are generally slower but give better yields.The diastereoselectivity of the present "flash" dihydroxylation, anti to the existing α-stereogenic center, with cycloalkenes is excellent whereas that with acyclic alkenes is moderate to poor.Sodium metaperiodate is still the best co-oxidant for the catalytic reaction.Aqueous acetonitrile (approximately 86percent) as an alternative solvent system was found to give better yields of 1,2-diols than the original solvent system in some cases. - Keywords: alkenes, catalysis, dihydroxylations, electrophilicity, ruthenium compounds.

First enantiospecific syntheses of crotepoxide and iso-crotepoxide from (-)-quinic acid

The optically active crotepoxide 1 and iso-crotepoxide 2 have been constructed from quinic acid involving a singlet oxygen photooxygenation as the key step.