220623-07-4

Basic information

• Product Name: (1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane
• Synonyms: (1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane
• CAS NO: 220623-07-4
• Molecular Formula: C₁₇H₃₁NO₄Si
• Molecular Weight: 341.51784
• Mol File: 220623-07-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane(220623-07-4)
• EPA Substance Registry System: (1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane(220623-07-4)

Safety Data

• Hazardous Substances Data: 220623-07-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane serves as a valuable intermediate in organic synthesis. Its unique structure and protecting groups make it suitable for the preparation of complex molecules with multiple stereocenters, which are crucial in various pharmaceutical and chemical applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane is utilized as a key building block for the synthesis of bioactive compounds. Its ability to create complex molecules with precise stereochemistry allows for the development of innovative drugs with improved efficacy and selectivity.
Used in Chemical Research:
(1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane also plays a significant role in chemical research, particularly in the exploration of new synthetic methods and strategies. Its unique structure and protecting groups provide opportunities for the development of novel reactions and the investigation of stereoselective processes.

Upstream product

• 45214-91-3 (2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid 
• 30004-64-9 (dimethylamino)phenyloxosulfonium methylide 
• 81658-27-7 (S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 17342-08-4 (S)-Pyroglutaminol 
• 293297-95-7 (5S)-N-(tert-Butoxycarbonyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(phenylseleno)pyrrolidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 96014-55-0 Methyl (4S)-4-(N-(tert-Butoxycarbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)pentanoate 
• 39538-20-0 (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 5-methyl ester 
• 126587-35-7 methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-hydroxypentanoate 
• 106191-02-0 (S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 186581-53-3 diazomethane 

Downstream Products

• 1092506-43-8 {(1S,2S,5R)-3-[(2-methyl-5-phenyl-1,3-thiazol-4-yl)carbonyl]-3-azabicyclo[3.1.0]hex-2-yl}methanol 
• 1092506-44-9 C₁₇H₁₉N₃OS 
• 1092504-90-9 N-({(1S,2S,5R)-3-[(2-methyl-5-phenyl-1,3-thiazol-4-yl)carbonyl]-3-azabicyclo[3.1.0]hex-2-yl}methyl)-1,3-benzoxazol-2-amine 

Relevant articles and documents

CYCLOPROPYL PYRROLIDINE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to cyclopropyl proline bis-amide compounds which are antagonists of orexin receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which orexin receptors are involved.

Cyclopropanation reactions of pyroglutamic acid-derived synthons with akylidene transfer reagents

The cyclopropanation of unsaturated lactams 1 and 3 derived from pyroglutamic acid with nucleophilic alkylidene transfer reagents is investigated. Good-to-modest yields of cyclopropanes were obtained with most sulfur ylides explored. Syn/anti selectivity was found to be dependent on the synthon as well as the sulfur ylide. This cyclopropanation methodology is used in the synthesis of arginine and glutamic acid analogues.

NEW ROUTES TO THE SYNTHESES OF CIS-α-(CARBOXYCYCLOPROPYL)GLYCINES FROM L-GLUTAMIC ACID. CONFORMATIONALLY RESTRICTED ANALOGUES OF THE EXCITATORY NEUROTRANSMITTER L-GLUTAMIC ACID

Potent neuroactive amino acids, (2S,2S,4R) and (2S,3R,4S) isomers of α-(carboxycyclopropyl)glycines (CCG-III and CCG-IV), were synthesized from L-glutamic acid via a palladium(II) catalyzed cyclopropanation of the α,β-unsaturated pyrrolidone and γ-amino-δ-lactone derivatives, respectively.