293751-17-4

Basic information

• Product Name: (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate
• Synonyms: (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate
• CAS NO: 293751-17-4
• Molecular Weight: 603.628
• Mol File: 293751-17-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate(293751-17-4)
• EPA Substance Registry System: (2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate(293751-17-4)

Safety Data

• Hazardous Substances Data: 293751-17-4(Hazardous Substances Data)

Upstream product

• 14631-20-0 4-N-Acetylcytosine 
• 293751-03-8 1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 100-39-0 benzyl bromide 
• 293751-01-6 3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 

Downstream Products

• 1610605-73-6 ((1R,3R,4R,7S)-3-(4-amino-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methylmethanesulfonate 
• 1610605-66-7 ((1R,3R,4R,7S)-3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate 
• 293751-20-9 (1R,3R,4R,7S)-1-benzoyloxymethyl-7-benzyloxy-3-(cytosin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 221229-74-9 (1S,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane 
• 293751-19-6 (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonoxymethyl-3-(cytosin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 

Relevant articles and documents

A simplified and efficient route to 2′-O, 4′-C-methylene-linked bicyclic ribonucleosides (locked nucleic acid)

A novel efficient method for the synthesis of locked nucleic acid (LNA) monomers is described. The LNA 5′,3′-diols containing thymine, 4-N-acetyl- and 4-N-benzoylcytosine, 6-N-benzoyladenine, and 2-N-isobutyrylguanine as nucleobases were prepared via convergent syntheses. The method is based on the use of the common sugar intermediate 1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl- 5-O-methanesulfonyl-D-erythro-pentofuranose (8) that easily can be prepared from D-glucose in multigram scale. Four different nucleobases were stereoselectively coupled to 8 using a modified Vorbrueggen procedure to give the corresponding 4′-C-branched nucleoside derivatives. Subsequent ring closing furnished the protected LNA nucleosides. The 5′-O-mesyl groups were efficiently displaced by nucleophilic substitution using sodium benzoate. Saponification of the 5′-benzoates followed by catalytic removal of the 3′-O-benzyl groups afforded the free LNA diols. The exocyclic amino groups of adenosine and cytidine were selectively acylated to give 4-N-acetyl- or 4-N-benzoyl-LNA-C and 6-N-benzoyl-LNA-A. The isobutyryl group of guanine was retained during the preparation of 2-N-isobutyryl-LNA-G. The LNA-T diol and base-protected LNA diols can be directly converted into LNA-phosphoramidites for automated chemical synthesis of LNA containing oligonucleotides.

Chemoenzymatic convergent synthesis of 2'-o,4'-c-methyleneribonucleosides

Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2- O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully