312904-18-0

Basic information

• Product Name: (3R,4R,5S)-4-(acetylamino)-3-(l-ethylρroρoxy)-5-(2-ρropenylamino)-l- cyclohexene-1 -carboxylic acid ethyl ester
• Synonyms: (3R,4R,5S)-4-acetylamino-5-allylamino-3-(1-ethyl propoxy)-cyclohex-1-ene carboxylic acid ethylester;(3R,4R,5S)-4-(acetylamino)-3-(l-ethylpropoxy)-5-(2-propenylamino)-l-cyclohexene-1-carboxylic acid ethyl ester;(3R,4R,5S)-4-acetylamino-5-allylamino-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester
• CAS NO: 312904-18-0
• Molecular Formula: C19H32N2O4
• Molecular Weight: 352.474
• Mol File: 312904-18-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3R,4R,5S)-4-(acetylamino)-3-(l-ethylρroρoxy)-5-(2-ρropenylamino)-l- cyclohexene-1 -carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5S)-4-(acetylamino)-3-(l-ethylρroρoxy)-5-(2-ρropenylamino)-l- cyclohexene-1 -carboxylic acid ethyl ester(312904-18-0)
• EPA Substance Registry System: (3R,4R,5S)-4-(acetylamino)-3-(l-ethylρroρoxy)-5-(2-ρropenylamino)-l- cyclohexene-1 -carboxylic acid ethyl ester(312904-18-0)

Safety Data

• Hazardous Substances Data: 312904-18-0(Hazardous Substances Data)

Usage

Description

(3R,4R,5S)-4-(acetylamino)-3-(l-ethylρroρoxy)-5-(2-ρropenylamino)-lcyclohexene-1 -carboxylic acid ethyl ester is an ethyl ester compound with a cyclohexene-1-carboxylic acid core, featuring an acetylamino group, an ethyl group, a propoxy group, and a propenylamino group. This stereo-specific molecule has a unique arrangement of methyl groups in the 3rd, 4th, and 5th positions, as indicated by the (3R,4R,5S) designation. The presence of an acetylamino group suggests potential pharmaceutical or medicinal applications, while the ethyl ester moiety may influence its solubility and stability properties.

Uses

Used in Pharmaceutical Industry:
(3R,4R,5S)-4-(acetylamino)-3-(l-ethylρroρoxy)-5-(2-ρropenylamino)-lcyclohexene-1 -carboxylic acid ethyl ester is used as a potential pharmaceutical compound for its possible medicinal applications. The presence of the acetylamino group, a common functional group in drug molecules, indicates that this compound may have therapeutic properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3R,4R,5S)-4-(acetylamino)-3-(l-ethylρroρoxy)-5-(2-ρropenylamino)-lcyclohexene-1 -carboxylic acid ethyl ester is used for its potential to be developed into a drug molecule. The specific arrangement of functional groups and the stereochemistry of the molecule may contribute to its interaction with biological targets, making it a candidate for further research and development.
Used in Chemical Research:
(3R,4R,5S)-4-(acetylamino)-3-(l-ethylρroρoxy)-5-(2-ρropenylamino)-lcyclohexene-1 -carboxylic acid ethyl ester is also used in chemical research for studying the effects of its unique structure on various chemical and biological reactions. (3R,4R,5S)-4-(acetylamino)-3-(l-ethylρroρoxy)-5-(2-ρropenylamino)-lcyclohexene-1 -carboxylic acid ethyl ester's properties, such as solubility and stability, can be investigated to understand its potential applications in different fields.
Used in Drug Delivery Systems:
Similar to gallotannin, (3R,4R,5S)-4-(acetylamino)-3-(l-ethylρroρoxy)-5-(2-ρropenylamino)-lcyclohexene-1 -carboxylic acid ethyl ester could be employed in the development of novel drug delivery systems. Its unique structure and functional groups may allow for improved delivery, bioavailability, and therapeutic outcomes when used as a carrier for other active pharmaceutical ingredients.

Upstream product

• 877238-97-6 ethyl (3R,4S,5R)-3-(1-ethylpropoxy)-5-N-formylamino-4-methanesulfonyloxy-1-cyclohexene-1-carboxylate 
• 312904-17-9 ethyl (3R,4S,5R)-5-amino-3-(1-ethylpropoxy)-4-methanesulfonyloxy-1-cyclohexene-1-carboxylate 
• 332047-22-0 ethyl (3R,4S,5R)-5-N-formylamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate 
• 332047-18-4 ethyl (3R,4S,5R)-5-N-benzylideneamino-3-(1-ethylpropoxy)-4-methanesulfonyloxy-1-cyclohexene-1-carboxylate 
• 332047-17-3 ethyl (3R,4S,5R)-5-N-benzylideneamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate 
• 312904-11-3 ethyl (3R,4S,5R)-5-N-allyllamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate 
• 312904-12-4 ethyl (3R,4S,5R)-5-amino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate 
• 204254-96-6 (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 
• 108-24-7 acetic anhydride 
• 312904-15-7 ethyl (3R,4R,5S)-5-N-allylamino-4-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate 

Downstream Products

• 196618-13-0 oseltamivir 

Relevant articles and documents

Process for the preparation of 4,5-diamino shikimic acid derivatives

The present invention relates to a process for the preparation of a 4,5-diamino shikimic acid derivative of formula and pharmaceutically acceptable addition salts thereof wherein R1, R1′ are independent of each other H or alkyl, R2 is an alkyl and R3, R4 are independent of each other H or an alkanoyl, with the proviso that not both R3 and R4 are H. 4,5-diamino shikimic acid derivatives of formula I, especially the (3R,4R,5S)-5-amino-4-acetylamino-3-(1-ethyl-propoxy)-cyclohex-1-ene-carboxylic acid ethyl ester and its pharmaceutically acceptable additional salts are potent inhibitors of viral neuraminidase.

Process for the preparation fo 4,5-diamino shikimic acid derivatives

The invention provides a multistep synthesis for the preparation of 4,5-diamino shikimic acid derivatives of formula wherein R1, R2, R3 and R4 are defined in the specification, starting from furan. 4,5-Diamino s

New, azide-free transformation of epoxides into 1,2-diamino compounds: Synthesis of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu)

A new, azide-free transformation of the key precursor epoxide 6 to the influenza neuraminidase inhibitor prodrug oseltamivir phosphate (1, Tamiflu) is described. This sequence represents a new and efficient transformation of an epoxide into a 1,2-diamino compound devoid of potentially toxic and hazardous azide reagents and intermediates and avoids reduction and hydrogenation conditions. Using catalytic MgBr2·OEt2 as a new, inexpensive Lewis acid, the introduction of the first amino function was accomplished by opening of the oxirane ring with allylamine followed by Pd/C-catalyzed deallylation to the amino alcohol 16. The introduction of the second amino group was then accomplished via an efficient reaction cascade involving a domino sequence preferably utilizing a transient imino protection. Selective acetylation of the resulting diamine 17 was achieved under acidic conditions providing the crystalline 4-acetamido-5-N-allylamino-derivative 18, which upon deallylation over Pd/C and phosphate salt formation afforded drug substance 1. The overall yield of this route from 6 of 35-38% exceeds the yield of the azide-based process (27-29%) and does not require any chromatographic purification.