125517-82-0

Basic information

• Product Name: (4S,5S)-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)-D-galacto-pentitol
• Synonyms: (4S,5S)-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)-D-galacto-pentitol
• CAS NO: 125517-82-0
• Molecular Weight: 305.328
• Mol File: 125517-82-0.mol

Chemical Properties

• CAS DataBase Reference: (4S,5S)-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)-D-galacto-pentitol(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)-D-galacto-pentitol(125517-82-0)
• EPA Substance Registry System: (4S,5S)-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)-D-galacto-pentitol(125517-82-0)

Safety Data

• Hazardous Substances Data: 125517-82-0(Hazardous Substances Data)

Upstream product

• 125517-80-8 1',2',3',4',5'-penta-O-acetyl-1'-C-[(4S,5S)-1,2-dimethyl-4-nitrocyclohex-1-en-5-yl]-D-galacto-pentitol 
• 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 

Downstream Products

• 478866-90-9 (4S,5S)-5-hydroxymethyl-1,2-dimethyl-4-nitrocyclohex-1-ene 
• 125517-84-2 (4S,5S)-1-C-(1,2-dimethyl-4-nitrocyclohex-1-en-5-yl)carbaldehyde 
• 125488-63-3 (R)-3,4-Dimethyl-6-nitro-cyclohex-3-enecarbaldehyde 

Relevant articles and documents

Studies on the chemistry of sodium nitronates and nitronic esters derived from 5-glyco-4-nitro-1-cyclohexenes

Reactions of sodium nitronates derived from 5-glyco-4-nitro-1-cyclohexenes with D-galacto or D-manno sugar side-chains have been investigated. With acetic anhydride/pyridine, these salts suffered an intramolecular cyclization affording high yields of tetraacetylated isoxazoline N-oxides. Treatment of the latter compounds with sodium methoxide yielded, either the corresponding deacetylated derivative or a bicyclic oxime, depending on the configuration of the sugar side-chain. Furthermore, unstable nitronic acid 13 has been isolated by recrystallization of nitronate 10 in dimethylsulfoxide, as well as by reaction of this substance with cold aqueous sulfuric acid. By refluxing with trimethyl phosphite, the N-oxides 14 and 16 led to isoxazolines which, like their precursors, could be considered as acyclic C-nucleosides.

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