132194-22-0

Basic information

• Product Name: (2S)-5α-(2-Amino-6-bromo-9H-purine-9-yl)tetrahydrofuran-2α-methanol
• Synonyms: (2S)-5α-(2-Amino-6-bromo-9H-purine-9-yl)tetrahydrofuran-2α-methanol;2-Amino-6-bromo-9-(2,3-dideoxy-β-D-ribofuranosyl)-9H-purine
• CAS NO: 132194-22-0
• Molecular Formula: C₁₀H₁₂BrN₅O₂
• Molecular Weight: 314.13858
• Mol File: 132194-22-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 612.8°C at 760 mmHg
• Flash Point: 324.4°C
• Appearance: /
• Density: 2.14g/cm³
• Vapor Pressure: 7.13E-16mmHg at 25°C
• Refractive Index: 1.859
• CAS DataBase Reference: (2S)-5α-(2-Amino-6-bromo-9H-purine-9-yl)tetrahydrofuran-2α-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-5α-(2-Amino-6-bromo-9H-purine-9-yl)tetrahydrofuran-2α-methanol(132194-22-0)
• EPA Substance Registry System: (2S)-5α-(2-Amino-6-bromo-9H-purine-9-yl)tetrahydrofuran-2α-methanol(132194-22-0)

Safety Data

• Hazardous Substances Data: 132194-22-0(Hazardous Substances Data)

Usage

Description

(2S)-5α-(2-Amino-6-bromo-9H-purine-9-yl)tetrahydrofuran-2α-methanol is a complex organic chemical compound characterized by the presence of a purine base, a tetrahydrofuran ring, and a methanol group. The purine base, integral to nucleic acids such as DNA and RNA, features both a pyrimidine and an imidazole ring. The tetrahydrofuran ring serves as a saturated cyclic ether, often utilized as a solvent in chemical reactions, while the methanol group is a straightforward alcohol component. (2S)-5α-(2-Amino-6-bromo-9H-purine-9-yl)tetrahydrofuran-2α-methanol's intricate structure and the inclusion of the purine base suggest potential applications in pharmaceuticals, biochemistry, and organic synthesis.

Uses

Used in Pharmaceutical Industry:
(2S)-5α-(2-Amino-6-bromo-9H-purine-9-yl)tetrahydrofuran-2α-methanol is used as a potential pharmaceutical agent for its unique structure and the presence of the purine base, which may contribute to the development of new drugs targeting specific biological pathways.
Used in Biochemistry Research:
In biochemistry, this compound is used as a research tool to study the interactions of purine bases with other biomolecules, potentially leading to insights into nucleic acid functions and related biochemical processes.
Used in Organic Synthesis:
(2S)-5α-(2-Amino-6-bromo-9H-purine-9-yl)tetrahydrofuran-2α-methanol is utilized as an intermediate or building block in organic synthesis, particularly for the creation of complex organic molecules that may have specialized applications in various fields.
Further research and testing are required to fully explore the properties and potential uses of this compound, as its complex structure and the presence of the purine base may offer novel opportunities in multiple industries.

InChI:InChI=1/C10H12BrN5O2/c11-8-7-9(15-10(12)14-8)16(4-13-7)6-2-1-5(3-17)18-6/h4-6,17H,1-3H2,(H2,12,14,15)/t5-,6+/m0/s1

Upstream product

• 82499-03-4 2-amino-6-bromopurine 
• 5983-09-5 2',3'-Dideoxyuridine 
• 2004-07-1 2-Amino-6-chloropurine riboside 

Relevant articles and documents

Nucleic Acid Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogues

Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (α-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents.Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time.Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino- 2-fluoropurine riboside.Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH(-)) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds.Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides.Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides.A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses.New 13C NMR data for several types of unsaturated-sugar nucleosides are tabulated.These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.