phenyl N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamate

Base Information

• Chemical Name: phenyl N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamate
• CAS No.: 445417-49-2
• Molecular Formula: C₂₄H₂₅N₅O₉S
• Molecular Weight: 559.557
• Mol file: 445417-49-2.mol

Synonyms:phenyl N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamate

Chemical Property of phenyl N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamate

There total 9 articles about phenyl N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamate 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: 78.0%

phenoxycarbonyl tetrazole + 2′,3′,5′-tri-O-acetyl-2-methylthioadenosine (70255-65-1) → phenyl N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamate (445417-49-2)

Guidance literature:

In 1,4-dioxane; at 40 ℃; for 20h; Inert atmosphere;

DOI:10.1002/chem.201902411

Reference yield:

2-(methylthio)adenosine (4105-39-9) → phenyl N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamate (445417-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / pyridine / 3 h / 0 °C

2: 74 percent / dioxane / 12 h / 35 - 40 °C

With pyridine; In 1,4-dioxane;

DOI:10.1021/ja028015f

Reference yield:

2-methylthio-6-aminopurine (1198-83-0) → phenyl N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamate (445417-49-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 48 percent / SnCl₄ / nitromethane / 18 h / 20 °C

2: 92 percent / NaOMe / methanol / 2 h / 20 °C

3: 86 percent / pyridine / 3 h / 0 °C

4: 74 percent / dioxane / 12 h / 35 - 40 °C

With pyridine; sodium methylate; tin(IV) chloride; In 1,4-dioxane; methanol; nitromethane;

DOI:10.1021/ja028015f

upstream raw materials:

2′,3′,5′-tri-O-acetyl-2-methylthioadenosine

2-(methylthio)adenosine

1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose

2-methylthio-6-aminopurine

Downstream raw materials:

N-[[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester

N-[[9-(β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester

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

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