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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).

Enzymatic Synthesis of Therapeutic Nucleosides using a Highly Versatile Purine Nucleoside 2’-DeoxyribosylTransferase from Trypanosoma brucei

Pérez, Elena,Sánchez-Murcia, Pedro A.,Jordaan, Justin,Blanco, María Dolores,Manche?o, José Miguel,Gago, Federico,Fernández-Lucas, Jesús

, p. 4406 - 4416 (2018/09/14)

The use of enzymes for the synthesis of nucleoside analogues offers several advantages over multistep chemical methods, including chemo-, regio- and stereoselectivity as well as milder reaction conditions. Herein, the production, characterization and utilization of a purine nucleoside 2’-deoxyribosyltransferase (PDT) from Trypanosoma brucei are reported. TbPDT is a dimer which displays not only excellent activity and stability over a broad range of temperatures (50–70 °C), pH (4–7) and ionic strength (0–500 mM NaCl) but also an unusual high stability under alkaline conditions (pH 8–10). TbPDT is shown to be proficient in the biosynthesis of numerous therapeutic nucleosides, including didanosine, vidarabine, cladribine, fludarabine and nelarabine. The structure-guided replacement of Val11 with either Ala or Ser resulted in variants with 2.8-fold greater activity. TbPDT was also covalently immobilized on glutaraldehyde-activated magnetic microspheres. MTbPDT3 was selected as the best derivative (4200 IU/g, activity recovery of 22 %), and could be easily recaptured and recycled for >25 reactions with negligible loss of activity. Finally, MTbPDT3 was successfully employed in the expedient synthesis of several nucleoside analogues. Taken together, our results support the notion that TbPDT has good potential as an industrial biocatalyst for the synthesis of a wide range of therapeutic nucleosides through an efficient and environmentally friendly methodology.

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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