73189-09-0

Basic information

• Product Name: ethyl 6-O-acetyl-4-(N-cyclohexyl)methylamino-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside
• Synonyms: ethyl 6-O-acetyl-4-(N-cyclohexyl)methylamino-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside
• CAS NO: 73189-09-0
• Molecular Weight: 311.422
• Mol File: 73189-09-0.mol

Chemical Properties

• CAS DataBase Reference: ethyl 6-O-acetyl-4-(N-cyclohexyl)methylamino-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 6-O-acetyl-4-(N-cyclohexyl)methylamino-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside(73189-09-0)
• EPA Substance Registry System: ethyl 6-O-acetyl-4-(N-cyclohexyl)methylamino-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside(73189-09-0)

Safety Data

• Hazardous Substances Data: 73189-09-0(Hazardous Substances Data)

Upstream product

• 100-60-7 N-methylcyclohexylamine 
• 3323-72-6 ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 

Relevant articles and documents

The preparation of amino sugars and branched-chain sugars by palladium-catalyzed allylic substitution of alkyl hex-2-enopyranosides

Ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (1) in the presence of triphenylphosphine and a catalytic amount of tetrakis(triphenylphosphine)palladium(0) reacted with a variety of amines or with reactive methylene compounds to give high yields of products aminated or C-alkylated, respectively, in allylic position.Some analogous experiments were performed using the β-D-erythro anomer (2) and the α-D-threo epimer (3) of 1.The constitutions and configurations of the new products were established by means of mass spectra, 13C- and 1H-nmr spectra, and optical rotation data.The reactions of 1 were found to be highly regio- and stereoselective, giving almost exclusively 4-substituted 2-enopyranosides with retention of configuration, except in the case of dibenzylamine which produced a mixture of the corresponding enoside and its 2-substituted, 3,4-unsaturated isomer ahving the α-D-threo configuration.The reactions of 2 appeared slightly less selective although they, too, furnished mainly 4-substituted 2-enopyranosides with retention of configuration.Regioselectivity was low or lacking in two C-alkylations performed with 3, which gave mixtures of 4-substituted 2-enosides and 2-substituted 3-enosides.Some aspects of conformation and optical rotation in enopyranosides are discussed.