72598-06-2

Upstream product

• 25125-21-7 4-(hydroxymethyl)cyclopentene 
• 58101-60-3 methyl cyclopent-3-ene-1-carboxylate 

Downstream Products

• 36368-48-6 exo-2-Oxabicyclo<2.2.1>hept-6-yl Brosylate 
• 72598-07-3 syn-3-(Hydroxymethyl)-6-oxabicyclo<3.1.0>hexyl Brosylate 

Relevant academic research and scientific papers

Asymmetric syntheses of (1r,3R,4S)- and (1s,3R,4S)-(3,4-difluorocyclopentyl)-alanine derivatives

By employing a sequence of epoxide opening, asymmetric alkylation, and fluorination, polyfluorinated cyclopentylamino acids with defined stereochemistries were prepared.

A flexible, efficient synthesis of (±)-carbocyclic phosphonic acid nucleoside derivatives

An efficient and flexible synthesis of cyclopentane and hydroxylated cyclopentane phosphonic acid analogues is described. The key step involves the opening of an epoxide with either a nucleoside base or a selenyl anion to access the target molecules.

Concerning the synthesis and enantioselective rearrangements of episulfoxides

A novel synthesis of episulfoxides having the norbornane skeleton is possible by use of a rhodium catalyst to effect SO transfer from from-stilbene episulfoxide to norbornene or norbornadiene. Analogous Rh2(OAc)4 catalysed sulfur transfer to these alkenes is also possible using propylene sulfide as the sulfur source. These methods did not give useful yields of products with alternative types of alkene substrate. A novel type of chiral lithium amide base reaction, involving the rearrangement of certain types of symmetrical ring-fused episulfoxides, gives alkenyl sulfoxide products in up to 88% ee. The structures of the products, including absolute stereochemistry, were assigned based on X-ray crystal structure determinations. The Royal Society of Chemistry 2000.

Highly Enentioselective Rearrangement of a meso-Epoxide to an Allyl Alcohol for Carbocyclic Nucleoside Synthesis: an Internal Alkoxide Effect

The synthesis of enantiomeric cis-4-(hydroxymethyl)cyclopent-2-ene-1-ols 2 and 3 (R=H) via a highly enantioselective rearrangement of cis-6-oxabicyclohexane-3-methanol 4 (R=H) using the dilithium salts of (+)- or (-)-norephedrine is described.

An asymmetric synthesis of (-)-carbovir

Enantioselective deprotonation of trans-4-t-butyldimethylsiloxymetyl-1,2-epoxycyclopentane (trans-4) by a chiral lithium amide, lithium (S)-2-(pyrrolidin-1-ylmethyl)pyrrolidide (1), afforded (1S,4S)-trans-4-t-butyldimethylsiloxymethyl-2-cyclopenten-1-ol (trans-7) in 83% ee. Alcohol trans-7 was easily transformed to (-)-carbovir, an anti-HIV carbocyclic nucleoside.

Concise Racemic and Highly Enantioselective Approaches to Key Intermediates for the Syntheses of Carbocyclic Nucleosides and pseudo-Ribofuranoses: Formal Syntheses of Carbovir

A regio- and stereo-specific synthesis of cis-(+/-)-3-acetoxy-5-(acetoxymethyl)cyclopentene 3 from cyclopent-3-enecarboxylic acid 4 via a bromolactonisation strategy is described.Pd-catalysed coupling of the cis-(+/-)-diacetate 3 with 2-amino-6-chloropurine or 2,6-diaminopurine leads to the formal syntheses of carbovir 1.A synthesis of the (1R)-cis-diacetate 15 (R = Ac) is described via a highly enantioselective rearrangement of cis-6-oxabicyclohexane-3-methanol 13 (also prepared from the acid 4) using the dilithium salt of (1S,2R)-norephedrine.

Synthesis and Solvolysis of syn- and anti-(6-Oxabicyclohex-3-yl)methyl p-Bromobenzenesulfonates

syn- and anti-3-(Hydroxymethyl)-6-oxabicyclohexanes (3a and 4a) have been prepared and the solvolysis rates of their p-bromobenzenesulfonate esters have been determined in aqueous ethanol.The solvolysis rate of 3c was found to be ca. 1E4-1E5 times faster than the rate of its anti epimer 4c but, unexpectedly, of similar order to the solvolysis rate of 6c.Both 3c and 6c yielded the same mixture of products, 6a and 6b, exclusively.The α- and β-deuterium isotope effects on the solvolysis of 5c and 3c-3-d were 1.034 and 1.084 per deuterium atom, respectively.Solvoly sis of 6c-6-d showed an α-isotope effect of 1.086.Also, it yielded a mixture of exo-substitution products with an equal distribution of the deuterium atom at C1 and C6.On the basis of these experimental data, solvolysis of 3c and 6c must have proceeded by way of the common oxonium ion intermediate (7) which arises from participation of the nonbonded electrons on the oxygen atom.The solvolysis rate of 4c is of similar magnitude to those of 1c and 2c; solvolysis yielded 80percent substitution products and thus was interpreted to proceed via a solvent-assisted ionization pathway.