97036-28-7

Basic information

• Product Name: (2S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(3-thienyl)acetonitril
• Synonyms: (2S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(3-thienyl)acetonitril
• CAS NO: 97036-28-7
• Molecular Weight: 328.435
• Mol File: 97036-28-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(3-thienyl)acetonitril(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(3-thienyl)acetonitril(97036-28-7)
• EPA Substance Registry System: (2S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(3-thienyl)acetonitril(97036-28-7)

Safety Data

• Hazardous Substances Data: 97036-28-7(Hazardous Substances Data)

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 143-33-9 sodium cyanide 
• 35019-66-0 (4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine 
• 97036-24-3 (4S,5S)-(+)-2,2-Dimethyl-4-phenyl-5-<(3-thienylmethylen)amino>-1,3-dioxan 

Downstream Products

• 1194-86-1 L-(+)-2-(3-Thienyl)glycin 
• 97101-16-1 (2S)-(-)-2-<(1S,2S)-(2-Hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-2-(3-thienyl)essigsaeure 

Relevant articles and documents

Nonproteinogenic Amino Acids, III. - Syntheses of the Enantiomerically Pure 2-(2-Thienyl)- and 2-(3-Thienyl)glycines. - Molecular Structure of the Intermediate Schiff's Bases

The syntheses of enantiomerically pure D-(-)- and L-(+)-2-(2-thienyl)- and 2-(3-thienyl)glycines (6a-d) are described.Preparing the amino nitriles 4 directly from 2-thiophenecarbaldehyde (1a) or 3-thiophenecarbaldehyde (1b), respectively, and (4S,5S)-(+)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane (2), and hydrocyanic acid (one-step procedure), the aminonitriles 4a and 4b, respectively, are formed in excess.By crystallization they are obtained diastereomerically pure leading to enantiomerically pure D-amino acids 6a and 6b.If, however, the intermediate Schiff's bases 3 are isolated as crystals and then converted with hydrocyanic acid into the respective aminonitriles 4 (two-step procedure), the diastereomeric aminonitriles 4c and 4d, respectively, crystallize resulting in enantiomerically pure L-amino acids 6a and 6d.X-ray structure analyses of the Schiff's bases 3c and 3e revealed the previously postulated E-configuration of the C=N bond and its chiral shielding by the phenyl substituent at C4.