Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate

Base Information

• Chemical Name: Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate
• CAS No.: 33422-70-7
• Molecular Formula: C19H23N5O9
• Molecular Weight: 465.42
• Mol file: 33422-70-7.mol

Synonyms:[9-(tri-O-acetyl-β-D-ribofuranosyl)-9H-purin-6-yl]-carbamic acid ethyl ester;Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-ethoxycarbonylamino-purin-9-yl)-tetrahydro-furan-3-yl ester;O2',O3',O5'-triacetyl-N6-ethoxycarbonyl-adenosine;N6-(ethoxycarbonyl)-2',3',5'-tri-O-acetyladenosine;

Chemical Property of Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate

Chemical Property:

• PSA: 170.06000
• LogP: 0.79160

Purity/Quality:

97% ^*data from raw suppliers

N-?(Ethoxycarbonyl)?-adenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-?(Ethoxycarbonyl)?-adenosine is an intermediate in synthesizing N6-(N-Threonylcarbonyl)adenosine (T405560). It is an essential modified nucleoside found in tRNA responsible for ANN codons in all three domains of life. It is also a biological marker in neoplastic diseases.

Technology Process of Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate

There total 5 articles about Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate 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: 85.0%

chloroformic acid ethyl ester (541-41-3) + triacetyladenosine (7387-57-7,953089-09-3) → ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate (33422-70-7)

Guidance literature:

With pyridine; at -10 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2014.04.048

Reference yield: 52.0%

8-ethoxy-3-(2',3',5'-tri-O-acetylribofuranosyl)imidazo<2,1-i>purine (96394-53-5) → ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate (33422-70-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃;

DOI:10.1021/jo00214a015

Reference yield:

N6-(1-ethoxy-2-chloroethylidene)-2',3',5'-tri-O-acetyladenosine (96394-56-8) → ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate (33422-70-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 39 percent / dimethylformamide / 8 h / 80 °C

2: 52 percent / m-chloro-perbenzoic acid (MCPBA) / CH₂Cl₂ / 0 °C

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00214a015

upstream raw materials:

8-ethoxy-3-(2',3',5'-tri-O-acetylribofuranosyl)imidazo<2,1-i>purine

chloroformic acid ethyl ester

triacetyladenosine

adenosine

Downstream raw materials:

N⁶-threonylcarbamoyladenosine

5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

5'-O-(4,4'-dimethoxytrityl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester

Refernces

• 1、 Schneider, Christina,Becker, Sidney,Okamura, Hidenori,Crisp, Antony,Amatov, Tynchtyk,Stadlmeier, Michael,Carell, Thomas. "Noncanonical RNA Nucleosides as Molecular Fossils of an Early Earth—Generation by Prebiotic Methylations and Carbamoylations". supporting information. p. 5943 - 5946. Retrieved 2018/04/30.
• 2、 Leonard, Nelson J.,Cruickshank, Kenneth A.. "Nucleoside Annelating Reagents: N-(tert-Butyloxycarbonyl)-2-bromoacetamide and 2-Chloroketene Diethyl Acetal". . p. 2480 - 2488. Retrieved 2007/10/02.