175221-03-1

Basic information

• Product Name: (1S,2S)-2-(((1R,2S,5R)-2-isopropyl-5-Methylcyclohexyloxy)carbonyl)cyclopropanecarboxylic acid
• Synonyms: (1S,2S)-2-(((1R,2S,5R)-2-isopropyl-5-Methylcyclohexyloxy)carbonyl)cyclopropanecarboxylic acid;(1S,2S)-Cyclopropane-1,2-dicarboxylic Acid MonoMenthyl Ester;(1S,2S)-2-(((1R,2S,5R)-2-isopropyl-5-Methylcyclohexyloxy)carbonyl)cyclopropanecarboxylic acid-5
• CAS NO: 175221-03-1
• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.34866
• Product Categories: Aliphatics, Miscellaneous Reagents
• Mol File: 175221-03-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 379.3±35.0 °C(Predicted)
• Appearance: /
• Density: 1.11±0.1 g/cm3(Predicted)
• PKA: 4.07±0.11(Predicted)
• CAS DataBase Reference: (1S,2S)-2-(((1R,2S,5R)-2-isopropyl-5-Methylcyclohexyloxy)carbonyl)cyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-2-(((1R,2S,5R)-2-isopropyl-5-Methylcyclohexyloxy)carbonyl)cyclopropanecarboxylic acid(175221-03-1)
• EPA Substance Registry System: (1S,2S)-2-(((1R,2S,5R)-2-isopropyl-5-Methylcyclohexyloxy)carbonyl)cyclopropanecarboxylic acid(175221-03-1)

Safety Data

• Hazardous Substances Data: 175221-03-1(Hazardous Substances Data)

Usage

Description

(1S,2S)-2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)carbonyl)cyclopropanecarboxylic acid is a complex organic compound with a unique molecular structure. It is characterized by its cyclopropanecarboxylic acid core, which is substituted with a carbonyl group connected to a cyclohexyloxy group. This cyclohexyloxy group has an isopropyl and a methyl substituent, making the molecule highly functional and versatile in its applications.

Uses

Used in Pharmaceutical Industry:
(1S,2S)-2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)carbonyl)cyclopropanecarboxylic acid is used as an intermediate in the synthesis of complex pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
Used in Synthetic Preparation:
(1S,2S)-2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)carbonyl)cyclopropanecarboxylic acid is used as a synthetic precursor for the preparation of biologically active compounds. For example, it was used in the synthetic preparation of Callipeltoside A, a compound that exhibits cytotoxicity against human bronchopulmonary non-small cell lung carcinoma. Its role in the synthesis of such compounds highlights its potential in contributing to the development of novel anticancer agents.

Upstream product

• 96149-00-7 (1S,2S)-cyclopropane-1,2-dicarboxylic acid bis-(1R,2S,5R)-(5-isopropyl-2-methyl-cyclohexyl) ester 
• 34212-59-4 bis(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl butanedioate 

Downstream Products

• 178685-01-3 (1S,2S)-2-chlorocarbonyl-cyclopropanecarboxylic acid (1R,2S,5R)-5-isopropyl-2-methyl-cyclohexyl ester 
• 329025-40-3 (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylate 
• 117857-93-9 (2S,1'S,2'S)-α-(2-carboxycyclopropyl)glycine 
• 329025-41-4 2-carbomenthyloxy (1S,2S)-cyclopropane-1-carboxaldehyde 
• 329025-42-5 (2S,1'S,2'S)-N-[(R)-α-phenylglycinol]-[2'-carbomenthyloxycyclopropyl]-glycinonitrile 
• 203209-15-8 (1S,2S)-2-[(R)-1-(4-Methoxy-benzyl)-2,5-dioxo-4-(9H-xanthen-9-ylmethyl)-imidazolidin-4-yl]-cyclopropanecarboxylic acid 4-methoxy-benzyl ester 
• 178898-43-6 (1S,2S-2-carboxycycloprop-1-yl) (2-(3-methylphenyl)ethyl) ketone 
• 178898-37-8 (1S,2S-2-carboxycycloprop-1-yl) (2,2-(diphenyl)ethyl) ketone 
• 201851-22-1 (5SR)-5-((1S,2S)-2-carboxycycloprop-1-yl)-5-[2-(3-methylphenyl)ethyl]imidazolidine-2,4-dione 
• 203208-44-0 (1S,2S)-2-(2-9H-Xanthen-9-yl-acetyl)-cyclopropanecarboxylic acid 
• 178684-67-8 (1S,2S)-2-(3-m-Tolyl-propionyl)-cyclopropanecarboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 201851-27-6 (5SR)-5-((1S,2S)-2-carboxycycloprop-1-yl)-5-(2,2-diphenylethyl)imidazolidine-2,4-dione 
• 178898-39-0 5R-5-(1S,2S-2-carboxycyclopropan-1-yl)-5-(2,2-(diphenyl)ethyl)imidazolidine-2,4-dione 
• 201851-15-2 (1S,2S)-2-[(R)-1-Amino-1-carboxy-2-(9H-xanthen-9-yl)-ethyl]-cyclopropanecarboxylic acid 

Relevant articles and documents

RADIOLABELED CANNABINOID RECEPTOR 2 LIGAND

The present invention relates to a compound of formula (I) wherein R1, R2, and R3 are defined as in the description and in the claims. The compound of formula (I) can be used as a radiolabeled ligand.

PYRIDINE AND PYRAZINE DERIVATIVES AS PREFERENTIAL CANNABINOID 2 AGONISTS

The invention relates to a compound of formula (I), wherein A1, A2 and R1-R5 are as defined in the description and in the claims. The compound of formula (I) can be used as cannabinoid 2 preferential agonist.

Callipeltoside A: Total synthesis, assignment of the absolute and relative configuration, and evaluation of synthetic analogues

The total synthesis of the novel antitumor agent callipeltoside A, as well as several analogues, is accomplished and allows assignment of the stereochemistry not previously established. A convergent strategy is employed wherein the target is dissected into three units - the core macrolactone, the sugar callipeltose, and a cyclopropyl bearing chain. The strategy for the synthesis of the macrolactone derives from employment of diastereoselective aldol reactions that emanate from an 11 carbon piece. The stereochemistry of the latter derives from the chiral pool and two asymmetric reactions - a ketone reduction using CBS-oxazaborolidine and a Pd catalyzed asymmetric allylic alkylation (AAA). The novelty of the latter protocol is its control of regioselectivity as well as absolute configuration. The trisubstituted olefin is generated using an alkene-alkyne coupling to create a trisubustituted olefin with complete control of geometry. The excellent chemo- and regioselectivity highlights the synthetic potential of this new ruthenium catalyzed process. The macrolactonization employs in situ formation of an acylketene generated by the thermolysis of a m-dioxolenone. Two strategies evolved for attachment of the side chain-one based upon olefination and a second upon olefin metathesis. The higher efficiency of the latter makes it the method of choice. A novel one pot olefin metathesis-Takai olefination protocol that should be broadly applicable is developed. The sugar is attached by a glycosylation by employing the O-trichloroacetimidate. This route provided both C-13 epimers of the macrolactone by using either enantiomeric ligand in the Pd AAA reaction. It also provided both trans-chlorocyclopropane diastereomers of callipeltoside A which allows the C-20 and C-21 configuration to be established as S and R, respectively. The convergent nature of the synthesis in which the largest piece, the macrolatone, require only 16 linear steps imparts utility to this strategy for the establishment of the structure-activity relationship. Initial biological testing demonstrates the irrelevance of the chloro substituent and the necessity of the sugar.