125488-63-3

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 
• 119479-73-1 (E)-3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-C-nitro-D-manno-hept-1-enitol 
• 125488-62-2 (4R,5R)-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)-D-manno-pentitol 
• 125488-62-2 (1R,2R,3R,4R)-1-((R)-3,4-Dimethyl-6-nitro-cyclohex-3-enyl)-pentane-1,2,3,4,5-pentaol 

Downstream Products

• 5973-71-7 3,4-dimethylbenzaldehyde 
• 82372-64-3 4,5-dimethylcyclohexa-1,4-diene-1-carbaldehyde 
• 478866-91-0 (4R,5R)-5-hydroxymethyl-1,2-dimethyl-4-nitrocyclohex-1-ene 

Relevant academic research and scientific papers

Reactions of hydroxylated sodium nitronates with acetic anhydride/pyridine

Reactions with Ac2O/Py of sodium nitronate salts derived from primary or secondary nitroalkanes bearing hydroxyl groups at γ or more remote positions have been studied. In all cases, the results could be explained through an acetic nitronic anhydride intermediate, whose evolution depends on conformational factors, and also on the type of the hydroxyl group.

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