3'-O-Methyl-D-adenosine

Base Information

• Chemical Name: 3'-O-Methyl-D-adenosine
• CAS No.: 10300-22-8
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.271
• NSC Number: 103062
• DSSTox Substance ID: DTXSID20908155
• Mol file: 10300-22-8.mol

Synonyms:3'-O-Methyladenosine;NSC 103062;

Chemical Property of 3'-O-Methyl-D-adenosine

Chemical Property:

• Melting Point: 177-178 °C
• Boiling Point: 623.8 °C at 760 mmHg
• PKA: 12.98±0.70(Predicted)
• Flash Point: 331 °C
• PSA: 128.54000
• Density: 1.84 g/cm³
• LogP: -0.74470
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 281.11240398
• Heavy Atom Count: 20
• Complexity: 349

Purity/Quality:

98%,99%, ^*data from raw suppliers

3'- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(OC(C1O)N2C=NC3=C(N=CN=C32)N)CO

Technology Process of 3'-O-Methyl-D-adenosine

There total 16 articles about 3'-O-Methyl-D-adenosine 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: 37.0%

trimethylsulphonium hydroxide (17287-03-5) + adenosine (58-61-7) → N6,O3'-methyladenosine (60037-52-7) + N6,O2'-methyladenosine (57817-83-1) + 2'-O-methyl adenosine (2140-79-6) + 3'-O-methyladenosine (10300-22-8)

Guidance literature:

With copper acetylacetonate; In N,N-dimethyl-formamide; at 70 ℃; for 1h; Further byproducts given;

DOI:10.1021/jo01307a026

Reference yield: 31.0%

trimethylselenonium hydroxyde (74230-06-1) + adenosine (58-61-7) → N6,O3'-methyladenosine (60037-52-7) + N6,O2'-methyladenosine (57817-83-1) + 2'-O-methyl adenosine (2140-79-6) + 3'-O-methyladenosine (10300-22-8)

Guidance literature:

With copper acetylacetonate; In methanol; N,N-dimethyl-formamide; at 70 ℃; for 0.5h; Further byproducts given;

Reference yield: 28.0%

trimethylsulphonium hydroxide (17287-03-5) + adenosine (58-61-7) → N6,O2'-methyladenosine (57817-83-1) + 2'-O,3'-O-dimethyladenosine (20649-46-1) + 2'-O-methyl adenosine (2140-79-6) + 3'-O-methyladenosine (10300-22-8)

Guidance literature:

With bis(acetylacetonate)nickel(II); In N,N-dimethyl-formamide; at 70 ℃; for 1h; Further byproducts given;

DOI:10.1021/jo01307a026

upstream raw materials:

trimethyl phosphite

adenosine

trimethylsulphonium hydroxide

trimethylphenylammonium hydroxide

Downstream raw materials:

N⁶,O^3'-methyladenosine

2'-O,3'-O-dimethyladenosine

2'-O-methyl adenosine

5'-O-[ (tert-butyl)(dimethyl)silyl]-N₆-[(4-methoxyphenyl)(diphenyl)methyl]-3'-O-methyladenosine

Refernces

• 1、 Yamauchi, Kiyoshi,Nakagima, Toru,Kinoshita, Masayoshi. "Selective 2'-O-Methylation of Pyrimidine-Ribonucleosides by Trimethylsulfonium Hydroxide in the Presence of Mg2+ and Ca2+ Ions". . p. 2947 - 2949. Retrieved 1986.
• 2、 Martin et al.. "-". . p. 1406,1407, 1411. Retrieved 1968.
• 3、 Martinez-Montero, Saul,Fernandez, Susana,Rodriguez-Perez, Tatiana,Sanghvi, Yogesh S.,Wen, Ke,Gotor, Vicente,Ferrero, Miguel. "Improved synthesis and isolation of 2'-O-methyladenosine: Effective and scalable enzymatic separation of 2'/3'-O-methyladenosine regioisomers". experimental part. p. 3265 - 3271. Retrieved 2009/12/24.
• 4、 Quaedflieg, Peter J. L. M.,Heiden, Arthur P. van der,Koole, Leo H.,Coenen, Annie J. J. M.,Wal, Sjoerd van der,Meijer, Emmo M.. "Synthesis and Conformational Analysis of Phosphate-Methylated RNA Dinucleotides". . p. 5846 - 5859. Retrieved 2007/10/02.