75096-60-5

Usage

Chemical family

Xylofuranose derivatives

Structural components

Xylofuranose ring, isopropylidene group, 4-methylbenzoyl group

Isopropylidene group position

C1

4-Methylbenzoyl group position

C5

Potential applications

Organic synthesis, medicinal chemistry

Ability

Modify reactivity and selectivity of chemical reactions

Usage

Building block for complex molecules with specific properties

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 532-20-7 α-D-xylofuranose 

Downstream Products

• 75096-61-6 1,2-O-isopropylidene-5-O-(4-methylbenzoyl)-3-O-trifluoromethanesulfonyl-α-D-xylofuranose 
• 75096-64-9 3-Azido-3-deoxy-1,2-di-O-acetyl-5-O-(4-methylbenzoyl)-β-D-ribofuranose 
• 75096-62-7 3-azido-1,2-O-isopropylidene-5-O-(4-methylbenzoyl)-3-deoxy-α-D-ribofuranose 
• 75096-63-8 4-Methyl-benzoic acid (3aR,6aR)-2,2-dimethyl-3a,6a-dihydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 
• 161110-15-2 N⁴-2-(4-nitrophenyl)ethoxycarbonyl-3'-deoxycytidi 
• 161109-94-0 N⁴,2'-di-N,O-acetyl-3'-deoxy-5'-O-(4-methylbenzoyl)-cytidine 
• 161110-00-5 N⁴-benzoyl-3'-deoxyribicytidine 
• 142823-65-2 1,2-di-O-acetyl-3-deoxy-5-O-(4-methylbenzoyl)-D-α,β-xylofuranose 
• 7057-33-2 3'-deoxycytidine 
• 86234-45-9 N⁴-benzoyl-5'-O-dimethoxytrityl-3'-deoxyribicytidine 
• 199528-80-8 1-[(2R,3S,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-(pyridin-2-yldisulfanyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 199528-79-5 1-[(2R,3S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-4-(pyridin-2-yldisulfanyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 199528-81-9 1-[(2R,3S,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-mercapto-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 199528-73-9 4-Methyl-benzoic acid (2R,3R,4S,5R)-4-acetoxy-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-benzoylsulfanyl-tetrahydro-furan-2-ylmethyl ester 

Relevant academic research and scientific papers

Design and synthesis of HIV-1 protease inhibitors. Novel tetrahydrofuran P2/P2′-groups interacting with Asp29/30 of the HIV-1 protease. Determination of binding from X-ray crystal structure of inhibitor protease complex

A series of HIV-1 protease inhibitors having new tetrahydrofuran P2/P2′ groups have been synthesised and tested for protease inhibition and antiviral activity. Six novel 4-aminotetrahydrofuran derivatives were prepared starting from commercially available

Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction

A practical synthetic route to the antitumor nucleoside, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine (ECyd, 1) from 1,2-O-isopropylidene-D-xylofuranose (3) has been developed. Since most of the compounds were obtained as crystals, the target ECyd was prepared without any chromatographic purification in 31% overall yield from compound 3. The isobutyryloxy group was found to be an effective leaving group at the anomeric position of the 3-β-C-ethynyl glycosyl donors in the key Vorbru?ggen glycosylation reaction. Using a similar procedure without chromatographic purification, the uracil congener EUrd [1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)uracil (2), which also has a potent antitumor effect, was synthesized from 3 in 39% overall yield.

Synthesis of 3′-thioribouridine, 3′-thioribocytidine, and their phosphoramidites

3′-Thio-3′-deoxyribonucleosides (U and C) have been synthesized via Vorbruggen-type glycosylation with 3-S-benzoyl-5-O-toluoyl-1,2-O-diacetylfuranose, which was obtained from 1,2-O-isopropylidene-5-O-toluoyl-3-O-trifluoromethanesulfonyl-α-D- xylofuranose. 3′-Thio-3′-deoxyuridine has been converted to its phosphoramidite. Copyright

Nucleosides. LVI. Synthesis and chemical modifications of 3'-deoxy- pyrimidine nucleosides

3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O- toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert- butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterized by elemental analyses and UV and 1H-NMR spectra.