937244-10-5

Basic information

• Product Name: N-Boc-cis-3,4-Methylene D-Proline
• Synonyms: N-Boc-cis-3,4-Methylene D-Proline;(1S,2R,5R)-3-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic Acid 3-(1,1-DiMethylethyl) Ester;(1S,2R,5R)-3-[(tert-Butoxy)carbonyl]-3-azabicyclo-[3.1.0]hexane-2-carboxylic acid
• CAS NO: 937244-10-5
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.25698
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 937244-10-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Boc-cis-3,4-Methylene D-Proline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-cis-3,4-Methylene D-Proline(937244-10-5)
• EPA Substance Registry System: N-Boc-cis-3,4-Methylene D-Proline(937244-10-5)

Safety Data

• Hazardous Substances Data: 937244-10-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 937244-10-5 differently. You can refer to the following data:
1. N-Boc-cis-3,4-Methylene D-Proline is used in the pyrrolidine carboxamides preparation and SAR as 11β-HSD1 inhibitors.
2. Used in the pyrrolidine carboxamides preparation and SAR as 11β-HSD1 inhibitors.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1051393-66-8 rac-cis(1S,2R,5R)-3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 
• 124-38-9 carbon dioxide 
• 936551-50-7 tert-butyl 6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate 

Relevant articles and documents

IMMUNOPROTEASOME INHIBITORS

Provided herein are compounds, such as a compound of Formula (I), as described herein, or a pharmaceutically acceptable salt thereof, that are immunoproteasome (such as LMP2 and LMP7) inhibitors. The compounds described herein can be useful for the treatment of diseases treatable by inhibition of immunoproteasomes. Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

Synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3- azabicyclo[3.1.0]hexane-2-carboxylic acid

A synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3- azabicyclo[3.1.0]hexane-2-carboxylic acid has been developed, thereby significantly shortening the known literature procedures for the syntheses of these unnatural amino acids. With a simple adjustment of the reaction conditions, we were able to obtain either pure cis or trans acid. Optical resolution was accomplished via diastereomeric salt formation or alternatively via chromatography on a chiral stationary phase. Finally, ab initio calculations gave an explanation for the observed cis selectivity in the initial step.