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64183-27-3

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64183-27-3 Usage

Description

2'-Fluoro-2'-deoxyadenosine is a modified nucleoside that consists of an adenosine molecule with a fluorine atom at the 2' position of the sugar moiety. This modification enhances the stability and activity of the molecule, making it a promising candidate for various applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
2'-Fluoro-2'-deoxyadenosine is used as a prodrug for 2-fluoroadenine, which is an active compound with potential therapeutic applications. The conversion of 2'-fluoro-2'-deoxyadenosine to 2-fluoroadenine is achieved through a deoxygenation process involving the reduction of the 2'-thiocarbonylimidazolide with (Tms)3SiH as a hydrogen donor. This prodrug approach allows for improved delivery and bioavailability of the active compound, enhancing its therapeutic potential.

Check Digit Verification of cas no

The CAS Registry Mumber 64183-27-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,1,8 and 3 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 64183-27:
(7*6)+(6*4)+(5*1)+(4*8)+(3*3)+(2*2)+(1*7)=123
123 % 10 = 3
So 64183-27-3 is a valid CAS Registry Number.

64183-27-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol

1.2 Other means of identification

Product number -
Other names 2'-Deoxy-2'-fluoroadenosine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:64183-27-3 SDS

64183-27-3Relevant articles and documents

Synthesis of Rovafovir Etalafenamide (Part IV): Evolution of the Synthetic Process to the Fluorinated Nucleoside Fragment

Siler, David A.,Calimsiz, Selcuk,Doxsee, Ian J.,Kwong, Bernard,Ng, Jeffrey D.,Sarma, Keshab,Shen, Jinyu,Curl, Jonah W.,Davy, Jason A.,Garber, Jeffrey A. O.,Ha, Sura,Lapina, Olga,Lee, Jisung,Lin, Lennie,Park, Sangsun,Rosario, Mary,St-Jean, Olivier,Yu, Guojun

, p. 1263 - 1274 (2021/05/29)

Fluorinated nucleoside 1 is a key starting material in the synthesis of rovafovir etalafenamide (2), a novel nucleotide reverse transcriptase inhibitor under development at Gilead Sciences for the treatment of HIV. While an initial manufacturing route enabled the production of 1 to support clinical development, alternative approaches were explored to further enhance manufacturing effectiveness, improve processing time, reduce cost, and minimize the environmental impact. Toward this end, two new routes were developed to a key synthetic intermediate, which was converted to 1 using a new protecting group strategy. The new chemistry led to improvements in the manufacturing process while reducing the overall process mass intensity (PMI).

Discovery of novel purine nucleoside derivatives as phosphodiesterase 2 (PDE2) inhibitors: Structure-based virtual screening, optimization and biological evaluation

Qiu, Xiaoxia,Huang, Yiyou,Wu, Deyan,Mao, Fei,Zhu, Jin,Yan, Wenzhong,Luo, Hai-Bin,Li, Jian

, p. 119 - 133 (2017/11/30)

Phosphodiesterase 2 (PDE2) has received much attention for the potential treatment of the central nervous system (CNS) disorders and pulmonary hypertension. Herein, we identified that clofarabine (4), an FDA-approved drug, displayed potential PDE2 inhibitory activity (IC50 = 3.12 ± 0.67 μM) by structure-based virtual screening and bioassay. Considering the potential therapeutic benefit of PDE2, a series of purine nucleoside derivatives based on the structure and binding mode of 4 were designed, synthesized and evaluated, which led to the discovery of the best compound 14e with a significant improvement of inhibitory potency (IC50 = 0.32 ± 0.04 μM). Further molecular docking and molecular dynamic (MD) simulations studies revealed that 5′-benzyl group of 14e could interact with the unique hydrophobic pocket of PDE2 by forming extra van der Waals interactions with hydrophobic residues such as Leu770, Thr768, Thr805 and Leu809, which might contribute to its enhancement of PDE2 inhibition. These potential compounds reported in this article and the valuable structure-activity relationships (SARs) might bring significant instruction for further development of potent PDE2 inhibitors.

Syntheses of 2′-deoxy-2′-fluoro-β-d-arabinofuranosyl purine nucleosides via selective glycosylation reactions of potassium salts of purine derivatives with the glycosyl bromide

Sivets, Grigorii G.

supporting information, p. 268 - 271 (2016/01/12)

Syntheses of 9-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-guanine (1) and -adenine (2) were accomplished from readily available 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-d-arabinofuranose (3). A new and efficient approach for the synthesis of 1-α-bromide was developed using the mild bromination of α-1-O-benzoate (3). Selective coupling reactions of the bromosugar with purine potassium salts followed by derivatization/and or deprotection of the intermediate blocked 2′-fluoro β-arabinonucleosides resulted in formation of the target compounds with high overall yields.

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