389626-30-6

Basic information

• Product Name: Cyclopropa[3,4]cyclopenta[1,2-d]-1,3-dioxole-4a(3aH)-methanol, tetrahydro-5-hydroxy-2,2-dimethyl-, (3aR,3bS,4aR,5S,5aS)- (9CI)
• Synonyms: Cyclopropa[3,4]cyclopenta[1,2-d]-1,3-dioxole-4a(3aH)-methanol, tetrahydro-5-hydroxy-2,2-dimethyl-, (3aR,3bS,4aR,5S,5aS)- (9CI)
• CAS NO: 389626-30-6
• Molecular Formula: C10H16O4
• Molecular Weight: 200.23164
• Product Categories: CYCLOPENTANE
• Mol File: 389626-30-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopropa[3,4]cyclopenta[1,2-d]-1,3-dioxole-4a(3aH)-methanol, tetrahydro-5-hydroxy-2,2-dimethyl-, (3aR,3bS,4aR,5S,5aS)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropa[3,4]cyclopenta[1,2-d]-1,3-dioxole-4a(3aH)-methanol, tetrahydro-5-hydroxy-2,2-dimethyl-, (3aR,3bS,4aR,5S,5aS)- (9CI)(389626-30-6)
• EPA Substance Registry System: Cyclopropa[3,4]cyclopenta[1,2-d]-1,3-dioxole-4a(3aH)-methanol, tetrahydro-5-hydroxy-2,2-dimethyl-, (3aR,3bS,4aR,5S,5aS)- (9CI)(389626-30-6)

Safety Data

• Hazardous Substances Data: 389626-30-6(Hazardous Substances Data)

Upstream product

• 155792-02-2 ethyl (1R,4R)-8,8-dimethyl-5-oxo-7,9-dioxatricyclo[4.3.0.0^[2,4]]nonane-4-carboxylate 
• 495397-74-5 ethyl (1R,4R)-5-hydroxy-8,8-dimethyl-7,9-dioxatricyclo[4.3.0.0^[2,4]]nonane-4-carboxylate 
• 155897-01-1 ethyl (1S,3R,4R,5S)-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate 
• 495397-65-4 ethyl (1S,3S,4S,5S)-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate 
• 25581-41-3 D-erythronolactone acetonide 
• 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 
• 495397-64-3 ethyl (4S,5S)-3-[2,2-dimethyl-5-vinyl(1,3-dioxolan-4-yl)]-2-diazo-3-oxopropanoate 
• 127666-07-3 4,5-Dideoxy-2,3-O-isopropylidene-L-erythro-pent-4-enoic acid 
• 127758-25-2 (4R,5S)-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methan-1-ol 
• 189996-60-9 2,3-O-isopropylidene-D-erythrose 
• 1026649-94-4 C₁₈H₂₁IO₅ 
• 155792-01-1 ethyl 2-diazo-3-(5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-oxopropanoate 
• 155792-00-0 ethyl 3-(5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-oxopropanoate 

Relevant articles and documents

A new synthetic route to (North)-methanocarba nucleosides designed as A3 adenosine receptor agonists

(Chemical Equation Presented) Activation of the A3 adenosine receptor (AR) is associated with cerebroprotective, cardioprotective, and anticancer effects. Among potent and selective A3 AR agonists are novel methanocarba adenosine analogues in which the conformation of a pseudo-ribose moiety is locked in the North (N) hemisphere of the pseudorotational cycle. 5′-Uronamide (N)-methanocarba nucleosides, such as MRS1898 and MRS2346, are examples of full agonists of the human A3 AR. An improved convergent approach from easily accessible 2,3-O-isopropylidene- D-erythrose (2b), and the combination of a strategic intramolecular cyclopropanation step plus the acid-catalyzed isomerization of an isopropylidene group, provided a suitable pseudosugar precursor (23) for the synthesis of MRS1898, MRS2346, and related analogues. This new synthetic route uses readily available building blocks and opens the way for the preparation of a variety of targets on a reasonable scale.

Recent advances in the synthesis of conformationally locked nucleosides and their success in probing the critical question of conformational preferences by their biological targets

The present work describes some recent approaches to the syntheses of three classes of locked-North nucleosides: β-D-ribo-, β-D-deoxyribo-, and β-D-dideoxy-ribonucleosides. The method developed for the latter class permitted access to a novel bicyclo[3.1.

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.