Adenosine, 3'-deoxy-3'-[(diethoxyphosphinyl)methyl]-, 5'-benzoate 2'-(O-phenyl carbonothioate)

Base Information

• Chemical Name: Adenosine, 3'-deoxy-3'-[(diethoxyphosphinyl)methyl]-, 5'-benzoate 2'-(O-phenyl carbonothioate)
• CAS No.: 90012-85-4
• Molecular Formula: C29H32N5O8PS
• Molecular Weight: 641.642
• Mol file: 90012-85-4.mol

Synonyms:

Chemical Property of Adenosine, 3'-deoxy-3'-[(diethoxyphosphinyl)methyl]-, 5'-benzoate 2'-(O-phenyl carbonothioate)

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Adenosine, 3'-deoxy-3'-[(diethoxyphosphinyl)methyl]-, 5'-benzoate 2'-(O-phenyl carbonothioate)

There total 4 articles about Adenosine, 3'-deoxy-3'-[(diethoxyphosphinyl)methyl]-, 5'-benzoate 2'-(O-phenyl carbonothioate) 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: 67.0%

9-(5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-β-D-ribofuranosyl)adenine (90012-84-3) + phenylcarbonochloridothioate (1005-56-7) → 9-(5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl)adenine (90012-85-4)

Guidance literature:

With dmap; In dichloromethane; for 12h; Ambient temperature;

Reference yield:

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-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl)adenine (90012-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / NH₂OH*AcOH / pyridine / Ambient temperature

2: 4-(dimethylamino)pyridine / CH₂Cl₂

With dmap; hydroxylamine acetate; In pyridine; dichloromethane;

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-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl)adenine (90012-85-4)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 4-(dimethylamino)pyridine / CH₂Cl₂

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

upstream raw materials:

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

phenylcarbonochloridothioate

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

Downstream raw materials:

9-(5-O-benzoyl-2,3-dideoxy-3-diethoxyphosphorylmethyl-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.