279248-94-1

Basic information

• Product Name: 3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 2',3'-lactone
• Synonyms: 3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 2',3'-lactone
• CAS NO: 279248-94-1
• Molecular Weight: 593.639
• Mol File: 279248-94-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 2',3'-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 2',3'-lactone(279248-94-1)
• EPA Substance Registry System: 3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 2',3'-lactone(279248-94-1)

Safety Data

• Hazardous Substances Data: 279248-94-1(Hazardous Substances Data)

Upstream product

• 279248-83-8 1,2,5-tri-O-acetyl-3-deoxy-3-[(ethoxycarbonyl)methyl]-D-ribofuranose 
• 279248-76-9 5-O-(tert-butyldimethylsilyl)-3-deoxy-3-[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-α-D-erythro-pentofuranose 
• 279248-82-7 1,2-di-O-acetyl-3-deoxy-3-[(ethoxycarbonyl)methyl]-5-O-methanesulfonyl-D-ribofuranose 
• 279248-80-5 5-O-acetyl-3-deoxy-3-[(ethoxycarbonyl)methyl]-1,2-O-isopropylidene-α-D-ribofuranose 
• 279248-77-0 3-deoxy-3-[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-α-D-erythro-pentofuranose 
• 178557-39-6 ethyl 2-[(3aR,5S,6R,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl]acetate 
• 66224-66-6 adenine 
• 103931-45-9 5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 279248-88-3 2',5'-di-O-acetyl-3'-deoxy-3'-[(ethoxycarbonyl)methyl]adenosine 

Downstream Products

• 268748-04-5 2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)adenosine 

Relevant articles and documents

Glucose-Derived 3′-(Carboxymethyl)-3′-deoxyribonucleosides and 2′,3′-Lactones as Synthetic Precursors for Amide-Linked Oligonucleotide Analogues

Treatment of a 1,2-O-isopropylidene-3-ketopentofuranose derivative (obtained from D-glucose) with [(ethoxycarbonyl)methylene]triphenylphosphorane and catalytic hydrogenation of the resulting alkene gave stereodefined access to 3-(carboxymethyl)-3-deoxy-D-ribofuranose derivatives. Esters of 5-O-acetyl- or 5-azido-5-deoxy-3-(carboxymethyl)-D-ribofuranose were coupled with nucleobases to give branched-chain nucleoside derivatives. Ester saponification and protecting group manipulation provided 2′-O-(tert-butyldimethylsilyl) ethers of 5′-azido-5′-deoxy- or 5′-O-(dimethoxytrityl) derivatives of 3′-(carboxymethyl)-3′-deoxyribonucleosides that are effective precursors for synthesis of amide-linked oligoribonucleosides.