328926-84-7

Upstream product

• 105-38-4 vinyl propionate 
• 677757-88-9 Acetic acid (4aS,7S,8aR)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-7-yl ester 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 677758-07-5 5-methyl-1-(2-phenyl-4a,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione 
• 262372-04-3 (1R,4S,5R)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine 
• 677757-95-8 9-(2-phenyl-4a,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-7-yl)-9H-purin-6-ylamine 

Relevant academic research and scientific papers

A straightforward stereoselective synthesis of D- and L-5-hydroxy-4-hydroxymethyl-2-cyclohexenylguanine

A novel and facile synthesis of 5-hydroxy-4-hydroxymethyl-2-cyclohexenylguanine 1 is described. The key steps involve a Diels-Alder reaction of ethyl (2E)-3-acetyloxy-2-propenoate 2 as dienophile with Danishefsky's diene 3 to build up the six-membered ring skeleton, a Fraser-Reid reductive rearrangement of the adduct using LiAlH4, and base-moiety introduction using a Mitsunobu reaction. Optically pure D- and L-1 were obtained via resolution of intermediate 7 with (R)-(-)-methylmandelic acid. The synthetic procedure toward racemic 1 consists of only five steps and has proven to be highly efficient toward the synthesis of cyclohexenyl nucleosides.

Synthesis of enantiomeric-pure cyclohexenyl nucleoside building blocks for oligonucleotide synthesis

Lipases were used for the resolution of (±) (4aR, 7R, 8aS)-2-phenyl-4a,7,8,8a-tetrahydro-4H-1,3-benzodioxine. This separation was carried out on preparative scale and used for the synthesis of eight phosphoramidites of cyclohexenyl nucleosides (D- and L-series).