181265-68-9

Upstream product

• 15679-27-3 (4S,5S)-4,5-bis(hydroxymethyl)cyclohexene 
• 17673-68-6 dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate 
• 141389-84-6 ((1S*,2S*)-cyclohex-4-ene-1,2-diyl)bis(methylene) dibenzoate 
• 141389-85-7 (4R,5R)-4,5-bis[(benzoyloxy)methyl]-1,2-epoxycyclohexane 

Downstream Products

• 181265-75-8 (1R,4S,5R)-1-acetoxy-4,5-bis[(benzoyloxy)methyl]cyclohex-2-ene 
• 1025988-64-0 C₂₇H₂₃ClN₄O₄ 
• 1025813-70-0 C₂₇H₂₄ClN₅O₄ 
• 1027283-06-2 C₂₇H₂₅N₅O₄ 
• 181265-82-7 [(1S,2S,5S)-5-(6-Amino-purin-9-yl)-2-hydroxymethyl-cyclohex-3-enyl]-methanol 
• 181489-29-2 [(1S,2S,5R)-5-(6-Amino-purin-9-yl)-2-hydroxymethyl-cyclohex-3-enyl]-methanol 
• 181265-86-1 2-Amino-9-((1S,4S,5S)-4,5-bis-hydroxymethyl-cyclohex-2-enyl)-1,9-dihydro-purin-6-one 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure bis(hydroxymethyl)-branched cyclohexenyl and cyclohexyl purines as potential inhibitors of HIV

The synthesis of the enantiomerically pure bis(hydroxymethyl)-branched cyclohexenyl and cyclohexyl purines is described. Racemic trans-4,5-bis(methoxycarbonyl)cyclohexene [(±)-6] was reduced with lithium aluminum hydride to give the racemic diol (±)-7. Resolution of (±)-7 via a transesterification process using lipase from Pseudomonas sp. (SAM-II) gave both diols in enantiomerically pure form. The enantiomerically pure diol (S,S)-7 was benzoylated and epoxidized to give the epoxide 9. Treatment of the epoxide 9 with trimethylsilyl trifluoromethanesulfonate and 1,5-diazabicyclo[5.4.0]undec-5-ene followed by dilute hydrochloric acid gave (1R,4S,5R)-4,5-bis[(benzoyloxy)methyl]1-hydroxycyclohex-2-ene (10). Acetylation of 10 gave (1R,4S,5R)-1-acetoxy-4,5-bis[(benzoyloxy)methyl]cyclohex-2-ene (11). (1R,4S,5R)-1-Acetoxy-4,5-bis[(benzoyloxy)methyl]cyclohex-2-ene (11) was converted to the adenine derivative 12 and guanine derivative 13 via palladium(0)-catalyzed coupling with adenine and 2-amino-6-chloropurine, respectively. Hydrogenation of 12 and 13 gave the corresponding saturated adenine derivative 14 and guanine derivative 15. (1R,4S,5R)-4,5-Bis[)benzoyloxy)methyl]-1-hydroxycyclohex-2-ene (10) was converted to the adenine derivative 16 and guanine derivative 17 via coupling with 6-chloropurine and 2-amino-6-chloropurine, respectively, using a modified Mitsunobu procedure. Hydrogenation of 16 and 17 gave the corresponding saturated adenine derivative 18 and guanine derivative 19. Compounds 12-19 were evaluated for activity against human immunodeficiency virus (HIV), but were found to be inactive. Further biological testings are underway.