85254-46-2

Upstream product

• 148132-86-9 (1R,2S,3S,4R,5S,6S)-1-Chloro-3,4-dihydroxy-5,6-di-O-isopropylidene-1,2-epoxycyclohexane 
• 127666-06-2 (3aS,7aS)-4-chloro-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 

Downstream Products

• 131550-34-0 (S)-2-Cyclohexyl-1-((4R,5S)-5-isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine 
• 141364-53-6 N'-[(S)-2-Cyclohexyl-1-((4R,5S)-5-isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-N,N-dimethyl-hydrazine 
• 127758-25-2 (4R,5S)-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methan-1-ol 
• 189996-60-9 2,3-O-isopropylidene-D-erythrose 
• 147879-42-3 N'-[(S)-1-((4R,5S)-5-Isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenyl-ethyl]-N,N-dimethyl-hydrazine 
• 147879-39-8 (3S,4S)-1-cyclohexyl-3,4-dihydroxy-6-methyl-5-hepten-2-one acetonide 
• 147879-44-5 (S)-1-((4R,5S)-5-Isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenyl-ethylamine 
• 143285-53-4 (4S,5R)-2,2-dimethyl-4-(2-methylpropan-1-yl)-5-<(1S)-1--2-cyclohexylethyl>-1,3-dioxolane 

Relevant academic research and scientific papers

FROM CHLOROBENZENE TO A CARBOHYDRATE IN TWO STEPS. A NEW CHEMOENZYMATIC SYNTHESIS OF 2,3-O-ISOPROPYLIDENE-D-ERYTHRURONOLACTONE

Controlled oxidation of chloroepoxide V with equivalents of sodium periodate furnished 2,3-O-isopropylidene-D-erythruronolactone (I) in 63percent yield.This procedure was augmented by combining the protection of diol III, the oxidation of acetonide IV to V, and the subsequent oxidative cleavage to I into one operation which yielded, on medium scale, the title lactone in 51percent yield.Detailed procedure of preparation and physical constants are provided for lactone I.

Improved practical synthesis of a prostaglandin and carbocyclic nucleoside synthon

An efficient, four step synthesis of chiral enone 2a [(+)-2,3-(isopropylidenedioxy)-4-cyclopentenone] from diol 1a (X = Cl), available from microbial oxidation of chlorobenzene, is described. This synthesis is a vast improvement over that previously reported and compares very favorably with others in the literature.

Microbial Oxidation of Chloroaromatics in the Enantiodivergent Synthesis of Pyrrolizidine Alkaloids: Trihydroxyheliotridanes

Both enantiomers of the pyrrolizidine alkaloid trihydroxyheliotridane 1 have been prepared in an efficient and stereocontrolled fashion in 10 steps.Key steps involve the microbial oxidation of chlorobenzene with Pseudomonas putida to afford chiral cyclohexadienediol 4 with high enantiomeric excess and its conversion to lactone 7, from which either enantiomer of azide 18 can be prepared.The azides are converted to the title compounds via a pyrroline annulation based on an intramolecuular azide-diene cycloaddition/thermal rearrangement.

AN ENANTIODIVERGENT APPROACH TO D- AND L-ERYTHROSE VIA MICROBIAL OXIDATION OF CHLOROBENZENE

D- and L-erythrose derivatives have been synthesized from chlorobenzene, providing for the conversion of undesired pollutants to synthetically useful chiral intermediates.The overall yields of the title compounds are compared to known preparation from ara