501665-22-1

Basic information

• Product Name: 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol
• Synonyms: 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol
• CAS NO: 501665-22-1
• Molecular Weight: 391.419
• Mol File: 501665-22-1.mol

Chemical Properties

• CAS DataBase Reference: 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol(501665-22-1)
• EPA Substance Registry System: 1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol(501665-22-1)

Safety Data

• Hazardous Substances Data: 501665-22-1(Hazardous Substances Data)

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 
• 217298-50-5 1',2',3',4',5'-penta-O-acetyl-1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol 

Relevant articles and documents

Preparation of enantiomerically pure 4-alkyl-5-formyl-4-nitrocyclohex-1-enes from 5-glyco-4-nitrocyclohex-1-enes

Base-catalyzed (TMG, DBU or TEA) asymmetric Michael reactions between 5-glyco-4-nitrocyclohex-1-enes 1a or 1b and a number of mono- or α,β-disubstituted electron-deficient alkenes yielded, in all cases, adducts in which the sugar side-chain and the added group on C-4 of the cyclohexene ring showed a trans-relationship. Furthermore, some of the adducts have been used to prepare enantiomerically pure 4-alkyl-5-formyl-4-nitrocyclohex-1-enes by a two-step process involving base-catalyzed (NaOMe) deacetylation of their respective sugar side-chains and subsequent oxidative cleavage (NaIO4). When reactions of 1a or 1b with dimethyl maleate, dimethyl fumarate or methyl trans-4-oxopentenoate were carried out with DBU (instead of TMG) as catalyst, there was in situ elimination of nitrous acid.

Stereoselective Michael addition reactions of 5-glyco-4-nitrocyclohex- 1-enes

Michael additions of 5-glyco-4-nitrocyclohex-1-enes (2 and 3) proceeded in a stereoselective way, leading in each case to single adducts in which the electron-deficient alkenes add on the C-4 of the cyclohexene rings, in a trans mode to the adjacent, sterically demanding, sugar side-chain. When dimethyl maleate or dimethyl fumarate and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were used, there was in situ elimination of nitrous acid, and the product consisted in a 1:1 mixture of the epimeric α,β-unsaturated esters 7.