229469-40-3

Basic information

• Product Name: 3,6-Dioxabicyclo[3.2.1]octane-5-methanol, 7-(6-chloro-9H-purin-9-yl)-8-(phenylmethoxy)-, acetate (ester), (1R,5R,7R,8S)-
• CAS NO: 229469-40-3
• Molecular Formula: C21H21ClN4O5
• Molecular Weight: 444.875
• Mol File: 229469-40-3.mol

Chemical Properties

• CAS DataBase Reference: 3,6-Dioxabicyclo[3.2.1]octane-5-methanol, 7-(6-chloro-9H-purin-9-yl)-8-(phenylmethoxy)-, acetate (ester), (1R,5R,7R,8S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Dioxabicyclo[3.2.1]octane-5-methanol, 7-(6-chloro-9H-purin-9-yl)-8-(phenylmethoxy)-, acetate (ester), (1R,5R,7R,8S)-(229469-40-3)
• EPA Substance Registry System: 3,6-Dioxabicyclo[3.2.1]octane-5-methanol, 7-(6-chloro-9H-purin-9-yl)-8-(phenylmethoxy)-, acetate (ester), (1R,5R,7R,8S)-(229469-40-3)

Safety Data

• Hazardous Substances Data: 229469-40-3(Hazardous Substances Data)

Upstream product

• 229469-35-6 3-O-benzyl-2-deoxy-2-(4,4'-dimethoxytriryloxymethyl)-4-C-hydroxymethyl-1-α-methyl-D-ribofuranose 
• 229469-33-4 3-O-benzyl-2-deoxy-2-(4,4'-dimethoxytrityloxymethyl)-1-α-methyl-D-ribofuranose 
• 229469-34-5 (2S,3S,4R,5S)-3-Benzyloxy-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methoxy-tetrahydro-furan-2-carbaldehyde 
• 229469-36-7 3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose 
• 229469-29-8 2-deoxy-2-methylene-1-α-methyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-ribofuranose 
• 229469-28-7 2-C,2-O-didehydro-1-α-methyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-ribofuranose 
• 229469-32-3 3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-hydroxymethyl-1-α-methyl-D-ribofuranose 
• 229469-31-2 3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-methylene-1-α-methyl-D-ribofuranose 
• 226214-50-2 (1S,3S,4R,8S)-8-benzyloxy-1-hydroxymethyl-3-methoxy-2,6-dioxabicyclo<3.2.1>octane 
• 229469-30-1 (2R,3S,5S)-2-Hydroxymethyl-5-methoxy-4-methylene-tetrahydro-furan-3-ol 
• 56607-40-0 methyl D-arabinofuranoside 
• 164454-52-8 methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside 
• 32865-86-4 6-chloro-9-trimethylsilylpurine 
• 229469-37-8 (1R,3S,4R,8S)-3-acetoxy-1-acetoxymethyl-8-benzyloxy-2,6-dioxabicyclo<3.2.1>octane 

Relevant articles and documents

Conformationally locked nucleosides. Synthesis and stereochemical assignments of 2'-C,4'-C-bridged bicyclonucleosides

1-α-O-Methyl-3-O,5-O-TIPDS-arabinose was converted, in multiple steps, to 2,6-dioxabicyclo[3,2,1]octane derivatives, which were condensed with silylated nucleoside bases to give the desired 2',4'-bridged bicyclonucleosides. In this article, synthesis and stereochemical assignments of the bicyclonucleosides are described.

Conformationally locked nucleoside analogs. Synthesis of 2'-Deoxy2′-C, 4′-C-bridged bicyclic nucleosides

1-a-Methylarabinose was converted, in three steps, to 2-deoxy-2-methyleneribose derivative 3, which was subjected to hydroboration to give 2-a-hydroxymethyl derivative 4 exclusively. 4 was converted to 2,4-bis(hydroxymethyl)ribose derivative 6 in four steps. Mesylation, detritylation, and ring closure, followed by hydrolysis of the mesyl group at OS, gave 3, 6-dioxabicyclo[3, 2, 1]octane derivative 8. After acetylation, 8 was coupled with silylated 6-chloropurine to give desired α- and β-bicyclic-sugar nucleosides. Copyright