143900-08-7

Basic information

• Product Name: (S)-(-)-3-methyl-4-<(2-tetrahydropyranyl)oxy>butyronitrile
• CAS NO: 143900-08-7
• Molecular Weight: 183.25
• Mol File: 143900-08-7.mol

Chemical Properties

• CAS DataBase Reference: (S)-(-)-3-methyl-4-<(2-tetrahydropyranyl)oxy>butyronitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-3-methyl-4-<(2-tetrahydropyranyl)oxy>butyronitrile(143900-08-7)
• EPA Substance Registry System: (S)-(-)-3-methyl-4-<(2-tetrahydropyranyl)oxy>butyronitrile(143900-08-7)

Safety Data

• Hazardous Substances Data: 143900-08-7(Hazardous Substances Data)

Upstream product

• 88588-59-4 (2S)-2-methyl-3-(tetrahydropyran-2-yloxy)propan-1-ol 
• 143-33-9 sodium cyanide 
• 88557-54-4 (2R)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl 4-methylbenzenesulfonate 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 187458-30-6 5-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-but-(Z)-ylidene]-4-methoxy-3-methyl-5H-furan-2-one 
• 187458-50-0 C₃₃H₃₈O₆S 
• 1027414-45-4 Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxy-4-methyl-5-oxo-2,5-dihydro-furan-2-yl)-2-methyl-butyl ester 
• 1026583-53-8 5-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methyl-butyl]-4-methoxy-3-methyl-5H-furan-2-one 
• 187458-29-3 (2S, 3S)-5-(tert-butyldiphenylsilyloxy)-3-methylpentane-1,2-diol 
• 169387-99-9 (S)-2-methyl-4-(tert-butyldiphenylsilyloxy)butanol 
• 63555-48-6 (-)-ircinianin 
• 64190-48-3 (S)-3-methyl-4-butanolide 

Relevant articles and documents

REVISION OF THE ABSOLUTE CONFIGURATION OF A-FACTOR; THE INDUCER OF STREPTOMYCIN BIOSYNTHESIS, BASING ON THE RECONFIRMED (R)-CONFIGURATION OF (+)-PARACONIC ACID

(+)-Paraconic acid was shown to be of (R)-configuration by its four-step conversion to (R)-(+)-3-methyl-4-butanolide.The absolute configuration at C-3 of A-factor was therefore revised to be R, since it was synthesized from (S)-(-)-paraconic acid.

Total synthesis of (-)-ircinianin and (+)-wistarin

(-)-Ircinianin (1), a cyclic furanosesterterpenetetronic acid isolated from a marine sponge (genus Ircinia), is synthesized in 17 steps from (S)-2-methylpropane-1,3-diol mono THP ether 10 and 3-furfural. The key step involves a NiCl2-CrCl2-mediated coupling reaction of iodotriene 9 with chiral aldehyde 8 in DMSO and subsequent intramolecular Diels-Alder reaction in one pot. Both reactions proceed very smoothly at room temperature and eventually give the cyclic product 30A possessing the desired cyclic skeleton of 1 in 60% yield. The structure of 30A is determined by X-ray crystallographic analysis. The stereochemistry of Diels-Alder reactions of 7A and another acyclic precursor 7B are discussed. The first total synthesis of (+)-wistarin (2) is accomplished in 55% yield by iodoether ring formation of 1 and hydrogenolysis of the iodide 33A. Based on the coupling constant in the proton NMR spectrum of 33A, the reported structure 2A is revised to 2B.