2-Hexynyladenosine

Base Information

• Chemical Name: 2-Hexynyladenosine
• CAS No.: 90596-73-9
• Molecular Formula: C₁₆H₂₁N₅O₄
• Molecular Weight: 347.374
• Mol file: 90596-73-9.mol

Synonyms:(2R,3R,4S,5R)-2-(6-Amino-2-hex-1-ynyl-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol;2-hexynyladenosine;2-(1-hexyn-1-yl)adenosine;

Chemical Property of 2-Hexynyladenosine

Chemical Property:

• PSA: 139.54000
• LogP: 0.14290

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Hexynyladenosine

There total 8 articles about 2-Hexynyladenosine 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: 89.0%

2-iodoadenosine (35109-88-7) + hex-1-yne (693-02-7) → 2-(1-hexynyl)adenosine (90596-73-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1016/S0960-894X(03)00020-9

Reference yield:

6-chloro-2-iodo-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine (5987-76-8) → 2-(1-hexynyl)adenosine (90596-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: liq. NH₃ / 20 °C

2: Et₃N; (Ph₃P)2PdCl₂; CuI / dimethylformamide / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; ammonia; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jm0109762

Reference yield:

2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (16321-99-6) → 2-(1-hexynyl)adenosine (90596-73-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / isoamyl nitrite, CH₂I₂ / 0.42 h / 80 °C / Heating

2: 90 percent / methanolic ammonia / 17 h / 60 °C

3: 85 percent / CuI, bis(triphenylphosphine)palladium dichloride, Et₃N / dimethylformamide / 1 h / 80 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diiodomethane; ammonia; triethylamine; isopentyl nitrite; In N,N-dimethyl-formamide;

DOI:10.1021/jm00080a007

upstream raw materials:

2-iodoadenosine

hex-1-yne

2-amino-6-chloro-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine

2-Amino-6-chloropurin

Refernces

• 1、 Lee, Jeewoo,Kim, Sung Eun,Lee, Ji Young,Kim, Su Yeon,Kang, Sang Uk,Seo, Seung Hwan,Chun, Moon Woo,Kang, Taehee,Choi, Soo Young,Kim, Hea Ok. "N-alkoxysulfamide, N-hydroxysulfamide, and sulfamate analogues of methionyl and isoleucyl adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases". . p. 1087 - 1092. Retrieved 2007/10/03.
• 2、 Cristalli, Gloria,Costanzi, Stefano,Lambertucci, Catia,Taffi, Sara,Vittori, Sauro,Volpini, Rosaria. "Purine and deazapurine nucleosides: Synthetic approaches, molecular modelling and biological activity". . p. 193 - 204. Retrieved 2007/10/03.