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

Base Information

• Chemical Name: N-[[9-(β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester
• CAS No.: 445417-51-6
• Molecular Formula: C₃₀H₄₃N₇O₁₀SSi
• Molecular Weight: 721.864
• Mol file: 445417-51-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about N-[[9-(β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester 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: 72.0%

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 (445417-50-5) → N-[[9-(β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester (445417-51-6)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 2h;

DOI:10.1021/jo025826t

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → N-[[9-(β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester (445417-51-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 48 percent / SnCl₄ / nitromethane / 16 h / 20 °C

2: 92 percent / sodium methoxide / methanol / 4 h / 25 °C

3: 86 percent / pyridine / 4 h / 0 °C

4: dioxane / 16 h / 35 - 40 °C

5: 75 percent / pyridine / 12 h / 35 - 40 °C

6: 72 percent / ammonia / methanol / 2 h / 20 °C

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

DOI:10.1021/jo025826t

Reference yield:

2′,3′,5′-tri-O-acetyl-2-methylthioadenosine (70255-65-1) → N-[[9-(β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester (445417-51-6)

Guidance literature:

Multi-step reaction with 3 steps

1: dioxane / 16 h / 35 - 40 °C

2: 75 percent / pyridine / 12 h / 35 - 40 °C

3: 72 percent / ammonia / methanol / 2 h / 20 °C

With ammonia; In 1,4-dioxane; pyridine; methanol;

DOI:10.1021/jo025826t

upstream 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

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

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

2-(methylthio)adenosine

Downstream raw materials:

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