176027-90-0 Usage
Description
Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1R,2R,5S,6R)-rel(9CI) is a complex organic compound with a unique bicyclic structure and multiple functional groups, including carboxylic acid and amino moieties. Its stereochemistry is defined by the (1R,2R,5S,6R) configuration, which is crucial for its potential applications and interactions with other molecules.
Uses
Used in Pharmaceutical Industry:
Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1R,2R,5S,6R)-rel(9CI) is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with specific therapeutic properties.
Used in Neuropharmacology:
In the field of neuropharmacology, Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1R,2R,5S,6R)-rel(9CI) is used as a precursor for the development of analogs of glutamate, such as LY 354740. These analogs act as potent and selective group II (mGlu2/3) receptor agonists, which may be useful for treating anxiety-related disorders by modulating the activity of mGlu receptors in the brain.
Used in Drug Delivery Systems:
Similar to gallotannin, Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1R,2R,5S,6R)-rel(9CI) can be employed in the development of novel drug delivery systems. Its unique structure and functional groups can be utilized to enhance the delivery, bioavailability, and therapeutic outcomes of various pharmaceutical compounds, particularly those targeting the central nervous system.
Check Digit Verification of cas no
The CAS Registry Mumber 176027-90-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,6,0,2 and 7 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 176027-90:
(8*1)+(7*7)+(6*6)+(5*0)+(4*2)+(3*7)+(2*9)+(1*0)=140
140 % 10 = 0
So 176027-90-0 is a valid CAS Registry Number.
176027-90-0Relevant articles and documents
Enantiospecific synthesis of (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane- 2,6-dicarboxylic acid by a modified Corey-Link reaction
Dominguez, Carmen,Ezquerra, Jesus,Baker, S. Richard,Borrelly, Stephane,Prieto, Lourdes,Espada, Modesta,Pedregal, Carmen
, p. 9305 - 9308 (1998)
(1S,2S,5R,6S)-2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740) was synthesised enantiospecifically from a sugar derived enantiomerically pure cyclopentenone. The α-amino acid stereogenic centre was formed by reacting the ketone with chloroform anion and then the alcohol so formed was reacted with sodium azide/DBU in methanol to give an azido ester. Critically, this modified Corey-Link reaction gives the opposite stereochemical outcome to the traditional Bucherer-Bergs and Strecker reactions. The azide was reduced and acylated, the 1,2 diol deoxygenated and the protecting groups removed to give LY354740 with an e.e.>98%.
Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives
Ohfune, Yasufumi,Demura, Takashi,Iwama, Seiji,Matsuda, Hiromi,Namba, Kosuke,Shimamoto, Keiko,Shinada, Tetsuro
, p. 5431 - 5434 (2007/10/03)
Efficient synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740: 1) and its structurally related analogs (-)-2 and (-)-3 has been accomplished starting with (1S,2R)-1-amino-2-hydroxycyclopentane- or cyclohexanecarboxylic acid (4 or 17 ) via an intramolecular cyclopropanation of α-diazo acetamide.
Preparation of bicyclic excitatory amino acids.
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, (2008/06/13)
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