Adenosine, 3'-deoxy-3'-[(diethoxyphosphinyl)methyl]-, 5'-benzoate

Base Information

• Chemical Name: Adenosine, 3'-deoxy-3'-[(diethoxyphosphinyl)methyl]-, 5'-benzoate
• CAS No.: 90012-84-3
• Molecular Formula: C22H28N5O7P
• Molecular Weight: 505.467
• Mol file: 90012-84-3.mol

Synonyms:

Chemical Property of Adenosine, 3'-deoxy-3'-[(diethoxyphosphinyl)methyl]-, 5'-benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Adenosine, 3'-deoxy-3'-[(diethoxyphosphinyl)methyl]-, 5'-benzoate

There total 4 articles about Adenosine, 3'-deoxy-3'-[(diethoxyphosphinyl)methyl]-, 5'-benzoate 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: 70.0%

9-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-α-D-ribofuranosyl)-6-benzamidopurine (31843-80-8) → 9-(5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-β-D-ribofuranosyl)adenine (90012-84-3) + Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-(ethoxy-hydroxy-phosphorylmethyl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Guidance literature:

With hydroxylamine acetate; In pyridine; Ambient temperature;

Reference yield: 65.0%

9-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-α-D-ribofuranosyl)-6-benzamidopurine (31843-80-8) → 9-(5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-β-D-ribofuranosyl)adenine (90012-84-3) + C20H23N5O7P(1-)*Na(1+) (133272-00-1)

Guidance literature:

With pyridine; hydroxylamine acetate; for 45h; Ambient temperature;

Reference yield:

1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-O-(diethoxyphosphonomethyl)-β-D-ribofuranose (31843-77-3) → 9-(5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-β-D-ribofuranosyl)adenine (90012-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / n-C₄F₉SO₃K/(Me₃Si)2NH/Me₃SiCl / acetonitrile

2: 70 percent / NH₂OH*AcOH / pyridine / Ambient temperature

With chloro-trimethyl-silane; hydroxylamine acetate; potassium nonaflate; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; acetonitrile;

upstream raw materials:

9-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-α-D-ribofuranosyl)-6-benzamidopurine

1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-O-(diethoxyphosphonomethyl)-β-D-ribofuranose

N-benzoyladenine

Downstream raw materials:

9-(5-O-benzoyl-2,3-dideoxy-3-diethoxyphosphorylmethyl-β-D-ribofuranosyl)adenine

9-(5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl)adenine

Refernces

• 1、 Morr, Michael,Ernst, Ludger,Grotjahn, Lutz. "2',3'-Dideoxy-3'-C-(phosphonomethyl)adenosine, the Phosphonate Analogue of 2'-Deoxyadenosine 3'-Phosphate". . p. 1665 - 1668. Retrieved 2007/10/02.