95463-56-2

Usage

InChI:InChI=1/C12H15BrN2O4/c13-2-1-7-5-15(12(19)14-11(7)18)9-3-8(6-16)10(17)4-9/h1-2,5,8-10,16-17H,3-4,6H2,(H,14,18,19)/b2-1+/t8-,9-,10+/m0/s1

Upstream product

• 91661-15-3 (E)-3-[1-((1S,3S,4S)-3-Hydroxy-4-hydroxymethyl-cyclopentyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acrylic acid 
• 62102-28-7 (+/-)-1-<(1β,3β,4β)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-(1H,3H)-pyrimidine-2,4-dione 
• 83967-03-7 1-((1S,3S,4S)-3-Hydroxy-4-hydroxymethyl-cyclopentyl)-5-iodo-1H-pyrimidine-2,4-dione 
• 95344-18-6 (E)-3-[1-((1S,3S,4S)-3-Hydroxy-4-hydroxymethyl-cyclopentyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acrylic acid methyl ester 
• 91661-15-3 (E)-3-<1,2,3,4-tetrahydro-1-<3α-hydroxy-4β-(hydroxymethyl)cyclopentan-1-yl>-2,4-dioxopyrimidin-5-yl>propenoic acid 
• 91661-12-0 1-<3β-hydroxymethyl-4α-(methoxymethoxy)cyclopentan-1-yl>pyrimidine-2,4-(1H,3H)-dione 
• 91661-11-9 1-<3β-dimethoxymethyl-4α-(methoxymethoxy)cyclopentan-1-yl>pyrimidine-2302,4-(1H,3H)-dione 
• 91661-10-8 N-carbamoyl>-3-ethoxypropenamide 
• 91661-14-2 ethyl (E)-3-<1,2,3,4-tetrahydro-1-<3α-hydroxy-4β-(hydroxymethyl)cyclopentan-1-yl>-2,4-dioxopyrimidin-5-yl>propenoate 
• 91661-09-5 (3S,4S)-3-Dimethoxymethyl-4-methoxymethoxy-cyclopentanecarboxylic acid 
• 62102-28-7 1-<3α-hydroxy-4β-(hydroxymethyl)-cyclopentan-1-yl>pyrimidine-2,4-(1H,3H)-dione 
• 648414-67-9 1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil 
• 98962-56-2 3-ethoxy-2-ethyl-acrylic acid 
• 120236-99-9 (-)-<(1R,2R,4R)-4-<(benzyloxy)methyl>-2-hydroxycyclopentyl>methyl benzoate 

Relevant academic research and scientific papers

New convergent synthesis of carbocyclic nucleoside analogues

Two convergent approaches towards the synthesis of carbocyclic nucleoside analogs will be described. Both approaches start from the stereochemically pure cyclopentenol 8 that has been prepared enantioselectively from an alkylated cyclopentadiene. Using these approaches, carbocyclic analogues of dT, FdU and BVdU have been prepared. Moreover, the conversion into the cycloSalpronucleotide and the corresponding nucleotide will be presented for one example.

A short high yielding synthesis of the potent anti-VZV carbocyclic nucleoside analogue carba-BVDU

A short high yielding synthesis of the potent anti-varicella-zoster virus (VZV) carbocyclic nucleoside analogue carba-BVDU 1 starting from aminodiol 2 is described. Reaction of 2 with acyl carbamate 3 and subsequent ring closure under acidic conditions afforded 5-ethyl-2'-deoxy-4'a-carbauridine 5. In situ acetylation of 5 afforded 3',5'-di-O-acetyl-5-ethyl-2'-deoxy-4'a-carbauridine 6 in 78% overall yield from 2. Radical bromination of 6 with either bromine or NBS and subsequent treatment with triethylamine gave an efficient conversion to 3',5'-di-O-acetyl-5-(E)-(2-bromovinyl)-2'-deoxy-4'a- carbauridine 7. Deacetylation of 7 afforded 1 in an overall 45-53% yield from 2.

A short, convergent synthesis of two chiral antiviral agents, (+) carbocyclic 2′-deoxy-5-[(E)-2-bromovinyl] uridine and (+) carbocyclic 2′-deoxyguanosine

Stereo selective microbial reduction of ketone 2 gave the alcohol 5 which was coupled under Mitsunobu conditions with the protected pyrimidine 7 and purine 10 to give on deprotection the chiral antiviral nucleosides (+) carbocyclic 2′-deoxy-5-[(E)-2bromov

Synthesis and Antiviral Activity of the Enantiomeric Forms of Carba-5-iodo-2'-deoxyuridine and Carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine

Both enantiomers of the carbocyclic analogues of 5-iodo-2'-deoxyuridine (14 and ent-14) and of (E)-5-(2-bromovinyl)-2'-deoxyuridine (16 and ent-16) were synthesized by using (+)- or (-)-endo-norborn-5-en-2-yl acetate or butyrate, respectively, as starting

Synthesis of the Carbocyclic Analogue of the Antiviral Nucleoside (E)-5-(2-Bromovinyl)-2'-deoxyuridine

The cyclopentanecarboxylic acid (1) was converted via the isocyanate (2) and the urea (5) into carbocyclic uridine (12).Similarly, the α- and β-epimers of carbocyclic 2'-deoxyuridine, (19a) and (19b), were synthesized from the acids (13).Compounds (19a) and (19b) were furhter modified to afford carbocyclic (E)-5-(2-bromovinyl)-2'-deoxyuridine (25b) and its α-epimer (25a), respectively.