62160-23-0

Usage

Chemical Properties

Off-White Solid

Uses

A guanosine analogue

InChI:InChI=1/C11H14N4O5/c12-11-13-8-4(9(19)14-11)1-2-15(8)10-7(18)6(17)5(3-16)20-10/h1-2,5-7,10,16-18H,3H2,(H3,12,13,14,19)/t5-,6-,7-,10-/m1/s1

Upstream product

• 80153-20-4 2-(Acetylamino)-3,7-dihydro-3-(isopropoxymethyl)-7-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 115479-40-8 4-chloro-7-{5′-O-[(1,1-dimethylethyl)-dimethylsilyl]-2′,3′-O-(1-methylethylidene)-β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidine-2-amine 
• 80153-19-1 3,7-Dihydro-3-(isopropoxymethyl)-2-methylthio-7-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 102690-95-9 5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl chloride 
• 115479-41-9 2-amino-4-methoxy-7-(2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 115479-42-0 2-Amino-4-methoxy-7-β-D-ribofuranosylpyrrolo<2,3-d>pyrimidine 
• 41028-66-4 1,5-anhydroribitol 
• 55726-00-6 (3R,4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol 
• 7355-55-7 2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 84955-31-7 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 120401-36-7 2-amino-4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 217309-46-1 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 
• 76567-71-0 2-Methylthio-7-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-4H-pyrrolo<2,3-d>pyrimidin-4-on 

Downstream Products

• 151072-88-7 2-<<(dimethylamino)methylidene>amino>-7-<5-O-(4-methoxytrityl)-2-O--β-D-ribofuranosyl>-3H-pyrrolo<2,3-d>pyrimidin-4(7H)-one 
• 141692-17-3 7-<5-O-(4-methoxytrityl)-β-D-ribofuranosyl>-2-<(2-methylpropanoyl)amino>-3H-pyrrolo<2,3-d>-pyrimidin-4(7H)-one 

Relevant academic research and scientific papers

C6–O-alkylated 7-deazainosine nucleoside analogues: Discovery of potent and selective anti-sleeping sickness agents

African trypanosomiasis, a deadly infectious disease caused by the protozoan Trypanosoma brucei spp., is spread to new hosts by bites of infected tsetse flies. Currently approved therapies all have their specific drawbacks, prompting a search for novel th

SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS

This invention provides expressible polynucleotides, which can express a target protein or polypeptide. Synthetic mRNA constructs for producing a protein or polypeptide can contain one or more 5′ UTRs, where a 5′ UTR may be expressed by a gene of a plant. In some embodiments, a 5′ UTR may be expressed by a gene of a member of Arabidopsis genus. The synthetic mRNA constructs can be used as pharmaceutical agents for expressing a target protein or polypeptide in vivo.

Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism

Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.

Phosphazole compounds

A class of substituted and unsubstituted nucleo-base analogs and related azoles, designated as "phosphazoles," is disclosed, certain preferred embodiments having the basic structure of STR1 Also disclosed are methods of making and using the new compounds.

A facile and improved synthesis of tubercidin and certain related pyrrolo[2,3-d]pyrimidine nucleosides by the stereospecific sodium salt glycosylation procedure [1]

A simple synthesis of tubercidin, 7-deazaguanosine and 2'-deoxy-7-deazaguanosine has been accomplished using the sodium salt glycosylation procedure. Reaction of the sodium salt of 4-chloro- and 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine, 3 and 4, respectively, with 1-chloro-2,3-O-isopropylidene,5-O-(t-butyl)dimethylsilyl-α-D-ribofur nose gave the corresponding protected nucleosides 6 and 7 with β-anomeric configuration. Deprotection of 6 provided 8, which on heating with methanolic ammonia gave tubercidin in excellent yield. Functional group transformation of 7, followed by deisopropylidenation gave 2-aminotubercidin and 2-amino-7-β-ribofuranosylpyrrolo[2,3-d]pyrimidine-4(3H)-thione. Treatment of 7 with 1N sodium methoxide followed by exposure to aqueous trifluoroacetic acid, and ether cleavage furnished 7-deazaguanosine. 2'-Deoxy-7-deazaguanosine and 2'-deoxy-7-deaza-6-thioguanosine were also prepared by using similar sequence of reactions employing 4 and 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose.

Synthesis of 2-Amino-3,7-dihydro-7-(β-D-ribofuranosyl)-4H-pyrrolopyrimindin-4-one - 7-Deazaguanosine - the Parent Compound of the Nucleoside Q

2-Amino-3,7-dihydro-7-(β-D-ribofuranosyl)-4H-pyrrolopyrimidin-4-one (1a), the parent compound of the rare nucleoside Q, has been synthesized using the pyrrolopyrimidine derivative 3a which was available by phase transfer glycosylation.N-3 al