401906-98-7

Basic information

• Product Name: 2-(2-aMino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylMethylene]-D-Altritol
• Synonyms: 2-(2-aMino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylMethylene]-D-Altritol
• CAS NO: 401906-98-7
• Molecular Formula: C₁₇H₁₈N₂O₆
• Molecular Weight: 346.33462
• Mol File: 401906-98-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2-aMino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylMethylene]-D-Altritol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-aMino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylMethylene]-D-Altritol(401906-98-7)
• EPA Substance Registry System: 2-(2-aMino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylMethylene]-D-Altritol(401906-98-7)

Safety Data

• Hazardous Substances Data: 401906-98-7(Hazardous Substances Data)

Usage

General Description

2-(2-aMino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylMethylene]-D-Altritol is a chemical compound that belongs to the class of purine nucleosides. It is a modified form of adenosine, a nucleoside found in DNA and RNA, with an additional anhydro and O-[(R)-phenylMethylene] modification on the deoxyribose sugar. 2-(2-aMino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylMethylene]-D-Altritol has potential biological and pharmaceutical applications, especially in the development of antiviral and antitumor drugs, due to its ability to inhibit viral and tumor cell growth by interfering with nucleic acid synthesis and replication. Additionally, it can also be used as a biochemical research reagent for studying nucleic acid structure and function.

Upstream product

• 66-22-8 uracil 
• 92283-88-0 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol 

Downstream Products

• 937031-47-5 1,5-anhydro-4,6-O-benzylidene-2-deoxy-3-O-(9-fluorenylmethoxycarbonyl)-2-(uracil-1-yl)-D-altro-hexitol 
• 852235-10-0 1,5-anhydro-4,6-O-benzylidene-2-deoxy-2-(5-iodouracil-1-yl)-D-altro-hexitol 
• 937031-51-1 1,5-anhydro-4,6-O-benzylidene-2-(cytosin-1-yl)-2-deoxy-D-altro-hexitol 

Relevant articles and documents

Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis

A new synthesis protocol for the preparation of hitherto unknown 1′,5′-anhydro-4′-amino-trityl/MMTr hexitol nucleosides has been developed. Key steps in the synthesis of the pyrimidine analogues (U and C) include the regioselective d-allo-hexitol oxirane and 2′,4′-anhydronucleoside ring opening by uracil and azide, respectively. A different strategy using a regioselective epoxide ring opening of d-gulo-oxirane, followed by a SN2 type of azidation reaction, has been adopted for the purine analogues (A and G). These compounds can be easily converted to 6′-phosphoramidites for the solid-phase synthesis of N4′ → P6′ phosphoramidates of amino hexitol nucleic acids (AHNA).

Synthesis of D-Altritol Nucleosides with a 3′ -O-Tert-Butyldimethylsilyl Protecting Group

Four D-altritol nucleosides with a 3′-O-tert- butyldimethylsilyl protecting group are synthesized (base moieties are adenine, guanine, thymine and 5-methylcytosine). The nucleosides are obtained by ring opening reaction of 1,5:2,3-dianhydro-4,6-O-benzylid

Synthesis of protected D-altritol nucleosides as building blocks for oligonucleotide synthesis

D-Altritol nucleosides with an adenine and uracil base moiety were obtained by nucleophilic opening of the epoxide ring of 1,5:2,3-dianhydro- 4,6-O-benzylidene-D-allitol using the sodium salt of the above mentioned bases. The use of a 2-trimethylsilylethyl protecting group for the O6- function of the guanine base offers a useful compromise between stability and acceptable alkylation yields of the N9-position if the guanine base. The cytosine nucleoside was synthesized starting from the uracil congener. The 3'-hydroxyl function was protected with a benzoyl group.