2'-O-Propargyladenosine

Base Information

• Chemical Name: 2'-O-Propargyladenosine
• CAS No.: 151390-97-5
• Molecular Formula: C13H15N5O4
• Molecular Weight: 305.293
• Mol file: 151390-97-5.mol

Synonyms:2'-O-(1-propyn-3-yl)adenosine;2'-O-propargyl adenosine;2'-O-propargyl-adenosine;2'-O-propargyladenosine;

Chemical Property of 2'-O-Propargyladenosine

Chemical Property:

• Boiling Point: 655.1±65.0 °C(Predicted)
• PKA: 13.00±0.70(Predicted)
• PSA: 128.54000
• Density: 1.65±0.1 g/cm3(Predicted)
• LogP: -0.74130

Purity/Quality:

99% ^*data from raw suppliers

2''-O-Propargyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-O-Propargyladenosine

There total 1 articles about 2'-O-Propargyladenosine 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: 45.0%

propargyl bromide (106-96-7) + adenosine (58-61-7) → 2'-O-(1-propyn-3-yl)adenosine (151390-97-5)

Guidance literature:

adenosine; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 5 - 50 ℃; Inert atmosphere;

propargyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; mineral oil; at 55 ℃; for 48h; Inert atmosphere;

DOI:10.1039/c0cc04667a

Reference yield: 95.0%

2'-O-(1-propyn-3-yl)adenosine (151390-97-5) + 4-bromo-benzaldehyde (1122-91-4) → 4-(3-(2'-O-adenosinyl)prop-1-yn-1-yl)benzaldehyde (1285573-86-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 55 ℃; for 0.5h; Microwave irradiation;

DOI:10.1039/c0cc04646a

Reference yield: 90.0%

2'-O-(1-propyn-3-yl)adenosine (151390-97-5) + Benzaldoxime (932-90-1) → 2'-O-((3-phenylisoxazol-5-yl)methyl)adenosine (1208867-32-6)

Guidance literature:

With bis-[(trifluoroacetoxy)iodo]benzene; In methanol; water; at 20 ℃; for 7h; regioselective reaction;

DOI:10.1039/c0cc04646a

upstream raw materials:

propargyl bromide

adenosine

Downstream raw materials:

2'-O-(3-(furan-2-yl)-propyn-3-yl)-6-N-benzoyladenosine

2'-O-(3-(furan-2-yl)-propyl)-6-N-benzoyladenosine

5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(3-(furan-2-yl)-propyl)-6-N-benzoyladenosine

5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(3-(furan-2-yl)-propyl)-6-N-benzoyladenosine-3'-O-(2-cyanoethyl N, N-diisopropylphosphoramidite)

Refernces

• 1、 Jawalekar, Anup M.,Op De Beeck, Marieke,Van Delft, Floris L.,Madder, Annemieke. "Synthesis and incorporation of a furan-modified adenosine building block for DNA interstrand crosslinking". supporting information; experimental part. p. 2796 - 2798. Retrieved 2011/05/05.