4'-Ethynyl-2-Fluoro-2'-Deoxyadenosine

Base Information

• Chemical Name: 4'-Ethynyl-2-Fluoro-2'-Deoxyadenosine
• CAS No.: 865363-93-5
• Molecular Formula: C₁₂H₁₂FN₅O₃
• Molecular Weight: 293.257
• European Community (EC) Number: 858-586-6
• UNII: QPQ082R25D
• DSSTox Substance ID: DTXSID601046407
• Nikkaji Number: J2.202.015C
• Wikipedia: Islatravir
• Wikidata: Q24977417
• NCI Thesaurus Code: C174896
• Metabolomics Workbench ID: 144541
• ChEMBL ID: CHEMBL517231
• Mol file: 865363-93-5.mol

Synonyms:2'-deoxy-4'-ethynyl-2-fluoroadenosine;4'-ethynyl-2-fluoro-2'-deoxyadenosine;islatravir;MK-8591;MK8591

Chemical Property of 4'-Ethynyl-2-Fluoro-2'-Deoxyadenosine

Chemical Property:

• Melting Point: 220.0-221.4 °C (decomp)
• Boiling Point: 669.2±65.0 °C(Predicted)
• PKA: 13.11±0.60(Predicted)
• PSA: 119.31000
• Density: 1.72±0.1 g/cm3(Predicted)
• LogP: -0.22710
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 293.09241742
• Heavy Atom Count: 21
• Complexity: 459

Purity/Quality:

97% ^*data from raw suppliers

Islatravir 99.94% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C#CC1(C(CC(O1)N2C=NC3=C(N=C(N=C32)F)N)O)CO
• Isomeric SMILES: C#C[C@]1([C@H](C[C@@H](O1)N2C=NC3=C(N=C(N=C32)F)N)O)CO
• Recent ClinicalTrials: Dose Ranging, Switch Study of Islatravir (ISL) and Ulonivirine (MK-8507) Once-Weekly in Virologically-Suppressed Adults With Human Immunodeficiency Virus Type 1 (HIV-1) [MK-8591-013]
• Recent EU Clinical Trials: A Phase 3, Randomized, Active-Controlled, Double-Blind Clinical Study to Evaluate the Efficacy and Safety of Oral Islatravir Once-Monthly as Preexposure Prophylaxis in Cisgender Men and Transgender Women Who Have Sex With Men, and Are at High Risk for HIV-1 Infection
• Uses: 4'-ethynyl-2-fluoro-2'-deoxyadenosine is a heterocyclic organic compound and can be used as pharmaceutical intermediates. MK-?8591 is a carbocyclic nucleoside reverse transcriptase translocation inhibitor and is used as an antiviral with potential use towards the treatment of HIV.

Technology Process of 4'-Ethynyl-2-Fluoro-2'-Deoxyadenosine

There total 62 articles about 4'-Ethynyl-2-Fluoro-2'-Deoxyadenosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

ammonium ((2R,3S)-2-ethynyl-3,5-dihydroxytetrahydrofuran-2-yl)methyl hydrogen phosphate + 2-fluoroadenine (700-49-2) → (2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol monohydrate (865363-93-5)

Guidance literature:

With triethanolamine hydrochloride; sodium hydroxide; manganese(ll) chloride; Sucrose; at 40 ℃; for 20h; pH=7.3 - 7.5; Enzymatic reaction;

Reference yield: 90.0%

(2R,3S,5R)-2-ethynyl-5-(2-fluoro-6-((trimethylsilyl)amino)-9H-purin-9-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate → (2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol monohydrate (865363-93-5)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 0 - 20 ℃;

DOI:10.1021/acs.orglett.7b00091

Reference yield: 87.0%

(2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-2-ethynyltetrahydrofuran-3-yl acetate (1332623-07-0) → (2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol monohydrate (865363-93-5)

Guidance literature:

(2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-2-ethynyltetrahydrofuran-3-yl acetate; With ammonium fluoride; In methanol; dichloromethane; at 20 ℃; for 43h;

With sodium hydroxide; In methanol; for 0.166667h; pH=10;

DOI:10.1271/bbb.120134

upstream raw materials:

(2R,3S,5R/S)-5-acetoxy-2-[(tert-butyldiphenylsilyloxy)methyl]-2-ethynyltetrahydrofuran-3-yl acetate

(2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-2-ethynyltetrahydrofuran-3-yl acetate

2-fluoroadenine

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

Refernces

• 1、 Ren, Sumei,Huffman, Mark A.,Whittaker, Aaron M.,Yang, Hao,Nawrat, Christopher C.,Waterhouse, David J.,Maloney, Kevin M.,Strotman, Neil A.. "Synthesis of Isotopically Labeled Anti-HIV Nucleoside Islatravir through a One-Pot Biocatalytic Cascade Reaction". . p. 516 - 521. Retrieved 2021.
• 2、 Johnson, Heather C.,Zhang, Shaoguang,Fryszkowska, Anna,Ruccolo, Serge,Robaire, Sandra A.,Klapars, Artis,Patel, Niki R.,Whittaker, Aaron M.,Huffman, Mark A.,Strotman, Neil A.. "Biocatalytic oxidation of alcohols using galactose oxidase and a manganese(iii) activator for the synthesis of islatravir". . p. 1620 - 1625. Retrieved 2021.
• 3、 -. "ADENOSINE DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME". . . Retrieved 2021/02/05.