139406-36-3

Upstream product

• 438625-50-4 1',2',3',4',5'-penta-O-acetyl-1'-C-[(4R,5R)-1,2-dimethyl-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol 
• 955378-01-5 (4S,5S)-1,2,3,4,5-penta-O-acetyl-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)-D-manno-pentitol 

Downstream Products

• 125488-63-3 (R)-3,4-Dimethyl-6-nitro-cyclohex-3-enecarbaldehyde 

Relevant academic research and scientific papers

Enantioselective Synthesis of Cyclohexene Nitro Aldehydes via Diels-Alder Reactions with Sugar Nitroolefins

Uncatalysed Diels-Alder reactions between (E)-1-deoxy-1-nitroalkenes derived from sugars and 2,3-dimethylbuta-1,3-diene yielded an easily separable mixture of the two possible diastereoisomeric adducts with good diastereofacial selectivity.In each case, preponderance of the major adduct has been rationalized in terms of the configuration of the chiral centre adjacent to the dienophilic double bond.Acid or alkaline deacetylation of the adducts, followed by degradative oxidation of the sugar side-chains, led to enantiomerically pure trans- or cis-cyclohexene nitro aldehydes.We also report on the easy elimination of the nitro group in nitro aldehydes, leading to cyclohexa-1,4-diene 11 or the aromatic aldehyde 12.

ENANTIOSELECTIVE SYNTHESIS OF CYCLOHEXENE NITROALDEHYDES

An enantioselective synthesis of cyclohexene nitroaldehydes 2e-5e has been effected, via Diels-Alder reaction with sugar nitroolefins as chiral dienophiles.Absolute configuration of products has been determined by X-ray crystallographic analysis and chemi