144985-81-9

Usage

General Description

"(1R,2R)-ethyl 1,2-bis(hydroxymethyl)cyclopropanecarboxylate" is a chemical compound with the molecular formula C9H16O4. It is a derivative of cyclopropane carboxylic acid, containing two hydroxymethyl groups attached to the cyclopropane ring. (1R,2R)-ethyl 1,2-bis(hydroxymethyl)cyclopropanecarboxylate is commonly used in organic and medicinal chemistry for the synthesis of various pharmaceuticals and bioactive molecules. Its stereospecificity (1R,2R) indicates the arrangement of substituent groups around the cyclopropane core, which is crucial for its chemical reactivity and pharmacological properties. The ethyl ester functionality allows for ease of handling and manipulation in chemical reactions, making it a versatile building block for the synthesis of complex organic compounds.

Upstream product

• 145032-58-2 ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 
• 105-53-3 diethyl malonate 

Downstream Products

• 205043-71-6 (1R,7R)-4,4-Dimethyl-3,5-dioxa-bicyclo[5.1.0]octane-1-carboxylic acid ethyl ester 
• 1384867-02-0 ethyl 2-(1-(hydroxymethyl)-2-(((4-methoxyphenyl)diphenylmethoxy)methyl)cyclopropyl)-acetate 
• 1384867-03-1 ethyl 2-(2-(((4-methoxyphenyl)diphenylmethoxy)methyl)-1-((tosyloxy)methyl)cyclopropyl)-acetate 
• 1384867-04-2 ethyl 2-(1-(fluoromethyl)-2-(((4-methoxyphenyl)diphenylmethoxy)methyl)cyclopropyl)-acetate 
• 1434876-01-3 [(1S,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octan-1-yl]methanol 
• 1434876-05-7 [(1R,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octan-1-yl]methyl methanesulfonate 
• 1434876-00-2 ethyl (1R,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octane-1-carboxylate 
• 1204820-70-1 ethyl (1R,5R)-3-(phenylmethyl)-3-azabicyclo[3.1.0]hexane-1-carboxylate 
• 1428427-13-7 C₂₄H₃₂O₄Si 
• 1428427-25-1 C₃₈H₄₇NO₄Si 
• 1428427-23-9 C₃₈H₄₃NO₄Si 
• 1428427-21-7 C₃₄H₃₉NO₃Si 
• 1428427-89-7 C₄₀H₄₃F₃N₂O₅ 

Relevant academic research and scientific papers

Synthesis of 1,1,2-trisubstituted cyclopropane nucleosides in enantiomerically pure forms

Due to the unique rigid and small steric feature of cyclopropane, cyclopropane nucleosides (CPNs) in which the ribose (deoxyribose) of nucleosides are replaced by a hydroxy-substituted cyclopropane, are of great biological interest. Novel 1,1,2-trisubstit

HETEROCYCLIC CARBOXYLIC ACIDS AS ACTIVATORS OF SOLUBLE GUANYLATE CYCLASE

The present invention relates to compounds of formula I: and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R5, R6, R7, R8, R9, B, V, W, X, Y, Z and m are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

METHOD FOR PREPARING CYCLOPROPANE DERIVATIVES

The present invention relates to the preparation of cyclopropane derivatives, in particular 2-amino-9-[[(1S,2R)-1,2-bis(hydroxymethyl)cyclopropyl]methyl]-4,8-dihydro-1H-purin-6-one, especially via the [(1S,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octan-1-yl]methanol intermediate.

Conformationally restricted GABA with bicyclo[3.1.0]hexane backbone as the first highly selective BGT-1 inhibitor

On the basis of the three-dimensional diversity-oriented conformational restriction strategy using key chiral cyclopropane units, we previously identified 3 ((2S,3R)-4-amino-3,4-methanobutyric acid) with a chiral trans-cyclopropane structure as a γ-aminobutyric acid (GABA) transporter inhibitor selective for GABA transporter (GAT) subtypes GAT-3 and BGT-1 (betaine/GABA transporter-1). Further conformational restriction of 3 with the rigid bicyclo[3.1.0]hexane backbone led to the successful development of the first highly potent and selective BGT-1 inhibitor 4 (IC50 = 0.59 μM). The bioactive conformation of 3 for BGT-1 was also identified.

Three-dimensional structural diversity-oriented peptidomimetics based on the cyclopropylic strain

Conformationally restricted peptidomimetics comprising eight stereoisomeric scaffolds with three-dimensional structural diversity were designed based on the structural features of cyclopropane, that is, cyclopropylic strain, which mimic wide-ranging tetra

METHOD FOR PREPARING CYCLOPROPANE DERIVATIVES

The present invention relates to the preparation of cyclopropane derivatives, in particular 2- amino-9-[[(1S,2R)-1,2- bis(hydroxymethyl) cyclopropyl] methyl]-4,8-dihydro-1H-purin-6-one, especially via the [(1S,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octan-1-yl]methanol intermediate.

A new nucleoside analogue with potent activity against mutant sr39 Herpes Simplex Virus-1 (HSV-1) Thymidine Kinase (TK)

Nucleoside analogues, such as penciclovir, ganciclovir, acyclovir, and their fluoro-substituted derivatives, have wide utility as antivirals. Among these analogues, FHBG (18F-Fluorohydroxybutylguanine) is a well-validated PET (positron emission

PIPERIDINE BASED UREAS AS NK1 ANTAGONISTS

The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein n is 1 or 2; useful in the treatment of conditions for which antagonism of NK1 receptor is beneficial.

Synthesis and antiviral activity of novel acyclic nucleosides: Discovery of a cyclopropyl nucleoside with potent inhibitory activity against herpesviruses

A series of acyclic nucleosides with two hydroxymethyl groups mimicking the 3'- and 5'-hydroxyl groups of the 2'-deoxyribose moiety were prepared and evaluated for their antiherpetic activity. Among those, 9-[[cis-1,2'- bis(hydroxymethyl)cycloprop-1'-yl]methyl]guanine (3) showed extremely potent antiviral activity against herpes simplex virus type-1 (HSV-1) with good selectivity. Both enantiomers of 3 were synthesized starting from chiral epichlorohydrins, and only one of the enantiomers with 1'S,2'R-configuration (3a) exhibited strong antiherpetic activity (IC50 of 0.020 μg/mL against HSV-1 Tomioka vs 0.81 μg/mL for acyclovir). Enantiomer 3a was also more inhibitory than acyclovir against varicella-zoster virus (VZV) but ineffective against human immunodeficiency virus (HIV). Compound 3a is phosphorylated by HSV-1 thymidine kinase (TK) very efficiently. The relationship between conformation and antiherpetic activity in this series of compounds is discussed.