793695-59-7

Basic information

• Product Name: Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate
• Synonyms: Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate
• CAS NO: 793695-59-7
• Molecular Formula: C₁₂H₁₈O₅
• Molecular Weight: 256.2949
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 793695-59-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate(793695-59-7)
• EPA Substance Registry System: Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate(793695-59-7)

Safety Data

• Hazardous Substances Data: 793695-59-7(Hazardous Substances Data)

Usage

Description

Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers and the presence of an isopropylidene group, which contributes to its specific chemical properties and reactivity.

Uses

Used in Pharmaceutical Synthesis:
Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate is used as a key intermediate in the synthesis of A3 adenosine receptor agonists and antagonists. These compounds have potential therapeutic applications in various diseases, including inflammatory and immune disorders, as well as neurodegenerative conditions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate serves as a valuable building block for the development of novel drug candidates. Its unique structure allows for the creation of new molecules with potential biological activities, contributing to the advancement of drug discovery and development efforts.
Used in Chemical Synthesis:
Beyond its applications in the pharmaceutical industry, Ethyl (1S,2R,3S,4S,5S)-2,3-O-(Isopropylidene)-4-hydroxybicyclo[3.1.0]hexanecarboxylate can also be utilized in other areas of chemical synthesis. Its reactivity and structural features make it a useful component in the preparation of various organic compounds, potentially leading to new materials and applications in different industries.

Upstream product

• 828935-09-7 ethyl (1S,2R,3R,4S,5S)-3,4-O-isopropylidene-2-hydroxybicyclo[3.1.0]hexane-1-carboxylate 
• 25581-41-3 D-erythronolactone acetonide 
• 189996-60-9 2,3-O-isopropylidene-D-erythrose 
• 127758-25-2 (4R,5S)-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methan-1-ol 
• 127666-07-3 4,5-Dideoxy-2,3-O-isopropylidene-L-erythro-pent-4-enoic acid 
• 116669-78-4 (4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 495397-63-2 ethyl (4S,5S)-3-[2,2-dimethyl-5-vinyl(1,3-dioxolan-4-yl)]-3-oxopropanoate 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 116780-31-5 (1R)-1-((4R,5S)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol 
• 495397-64-3 ethyl (4S,5S)-3-[2,2-dimethyl-5-vinyl(1,3-dioxolan-4-yl)]-2-diazo-3-oxopropanoate 
• 495397-65-4 ethyl (1S,3S,4S,5S)-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate 

Downstream Products

• 793695-72-4 (1'S,2'R,3'S,4'R,5'S)-4'-[6-(3-methylbenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidenebicyclo[3.1.0]haxane-1'-carboxylic acid ethyl ester 
• 793695-71-3 (1'S,2'R,3'S,4'R,5'S)-4'-[6-(2-methylbenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidenebicyclo[3.1.0]haxane-1'-carboxylic acid ethyl ester 
• 793695-98-4 (1aS,1bR,4aS,5R,5aS)-5-[6-(3-Bromo-benzylamino)-2-chloro-purin-9-yl]-3,3-dimethyl-tetrahydro-2,4-dioxa-cyclopropa[a]pentalene-1a-carboxylic acid methylamide 
• 793695-62-2 (1'S,2'R,3'S,4'R,5'S)-4'-[6-(3-fluorobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidenebicyclo[3.1.0]haxane-1'-carboxylic acid ethyl ester 
• 793695-75-7 (1'S,2'R,3'S,4'R,5'S)-4'-[6-(4-aminobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidenebicyclo[3.1.0]haxane-1'-carboxylic acid ethyl ester 
• 793695-63-3 (1'S,2'R,3'S,4'R,5'S)-4'-[6-(3-chlorobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidenebicyclo[3.1.0]haxane-1'-carboxylic acid ethyl ester 
• 793695-61-1 (1'S,2'R,3'S,4'R,5'S)-4'-[6-(3-bromobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidenebicyclo[3.1.0]haxane-1'-carboxylic acid ethyl ester 
• 793695-83-7 (1'S,2'R,3'S,4'R,5'S)-4'-[6-(3-chlorobenzylamino)-2-iodopurin-9-yl]-2',3'-isopropylidenebicyclo[3.1.0]hexane-1'-carboxylic acid ethyl ester 

Relevant articles and documents

COMPOUNDS TARGETING PRMT5

Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating diseases and/or conditions with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.

South (S)- and north (N)-methanocarba-7-deazaadenosine analogues as inhibitors of human adenosine kinase

Adenosine kinase (AdK) inhibitors raise endogenous adenosine levels, particularly in disease states, and have potential for treatment of seizures, neurodegeneration, and inflammation. On the basis of the South (S) ribose conformation and molecular dynamics (MD) analysis of nucleoside inhibitors bound in AdK X-ray crystallographic structures, (S)- and North (N)-methanocarba (bicyclo[3.1.0]hexane) derivatives of known inhibitors were prepared and compared as human (h) AdK inhibitors. 5′-Hydroxy (34, MRS4202 (S); 55, MRS4380 (N)) and 5′-deoxy 38a (MRS4203 (S)) analogues, containing 7- and N6-NH phenyl groups in 7-deazaadenine, robustly inhibited AdK activity (IC50 ～ 100 nM), while the 5′-hydroxy derivative 30 lacking the phenyl substituents was weak. Docking in the hAdK X-ray structure and MD simulation suggested a mode of binding similar to 5′-deoxy-5-iodotubercidin and other known inhibitors. Thus, a structure-based design approach for further potency enhancement is possible. The potent AdK inhibitors in this study are ready to be further tested in animal models of epilepsy.

Synthesis of ethyl (1S,2R,3S,4S,5S)-2,3-O-(isopropylidene)-4-hydroxy- bicyclo[3.1.0]hexane-carboxylate from l-ribose: A versatile chiral synthon for preparation of adenosine and P2 receptor ligands

Substitution of the ribose moiety of various nucleosides and nucleotides with the (N)-methanocarba ring system increases the potency and selectivity as ligands at certain subtypes of adenosine and P2 receptors. We have prepared a key intermediate in the synthesis of these derivatives, ethyl (1S,2R,3S,4S,5S)-2,3-O-(isopropylidene)-4-hydroxybicyclo[3.1.0] hexane-carboxylate (15), starting from L-ribose (8) as a readily available, enantiopure building block. L-ribose was converted to the corresponding 5′-iodo derivative (9), which was cleaved reductively with Zn. Improvements were made in subsequent steps corresponding to a published route to biologically important (N)-methanocarba 5′-uronamido nucleosides, and new steps were added to prepare related 5′-nucleotides. Copyright Taylor & Francis Group, LLC.