145032-59-3

Upstream product

• 205043-74-9 (1S,7R)-1-benzyloxymethyl-4,4-dimethyl-3,5-dioxabicyclo[5.1.0]octane 
• 205043-71-6 (1R,7R)-4,4-Dimethyl-3,5-dioxa-bicyclo[5.1.0]octane-1-carboxylic acid ethyl ester 
• 144985-85-3 (1R,2R)-1-benzyloxymethyl-2-hydroxymethylcyclopropane-1-methanol 
• 144985-81-9 ethyl (1R,2R)-1,2-bis(hydroxymethyl)-1-cyclopropanecarboxylate 
• 205043-72-7 (1S,7R)-4,4-dimethyl-3,5-dioxabicyclo[5,1,0]oct-1-yl methanol 
• 145032-58-2 ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 
• 105-53-3 diethyl malonate 
• 98-88-4 benzoyl chloride 
• 389626-36-2 {(1R,2R)-2-(hydroxymethyl)-2-[(trityloxy)methyl]cyclopropyl}methanol 
• 144985-86-4 (1S,2R)-{2-[(benzoyloxy)methyl]-1-[(benzyloxy)methyl]cycloprop-1-yl}methyl benzoate 

Relevant academic research and scientific papers

Bicyclo[3.1.0]hexanes from sugar-derived diazo compounds and iodonium ylides. Diastereocontrol and synthetic applications

The CuI and Rh2(OAc)4 catalyzed decomposition of ethyl 2-diazo-4,5-isopropylidenedioxy-3-oxo-6-heptenoate results in intramolecular cyclopropanation products with opposite diastereoselectivity. In contrast, decomposition of the respective iodonium ylide can proceed without catalysts to give the cyclopropanation products with diastereoselectivity unchangeable by the presence of CuI and Rh2(OAc)4, revealing thus, that in this particular case the reaction is an electrophilic addition of the iodonium center to the double bond. The synthetic importance of these reactions has been demonstrated by preparing a number of precursors of cyclopentyl, cyclopropyl and bicyclo[3.1.0]hexyl antiviral carbocyclic nucleosides.

Carbocyclic nucleoside precursors by intramolecular cyclopropanation of sugar-derived diazo compounds

Bicyclo[3.1.0]hexane derivatives, selectively prepared by intramolecular cyclopropanation of sugar-derived unsaturated diazo compounds, are common precursors for the sugar moiety of cyclopentane, cyclopropane and bicyclo[3.1.0]hexane nucleosides, such as aristeromycin, the carbocyclic analogue of neplanocin C and the nucleoside A-5021.

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.

Cyclopropane derivative

A cyclopropane derivative of formula (I) STR1 wherein B1 is a purine or pyrimidine residue, R1 and R2 are, independently, hydrogen or a protecting group for hydroxyl and each of k, m and n represents, independently, an int