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

Base Information

• Chemical Name: 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
• CAS No.: 445417-53-8
• Molecular Formula: C₅₇H₇₅N₇O₁₂SSi₂
• Molecular Weight: 1138.5
• Mol file: 445417-53-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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: 59.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 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 (445417-52-7) → 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 (445417-53-8) + N-[[9-(3'-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

Guidance literature:

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; With silver nitrate; In tetrahydrofuran; at 20 ℃; for 0.5h;

tert-butyldimethylsilyl chloride; With pyridine; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/jo025826t

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 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 (445417-53-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 48 percent / SnCl₄ / nitromethane / 16 h / 20 °C

2.1: 92 percent / sodium methoxide / methanol / 4 h / 25 °C

3.1: 86 percent / pyridine / 4 h / 0 °C

4.1: dioxane / 16 h / 35 - 40 °C

5.1: 75 percent / pyridine / 12 h / 35 - 40 °C

6.1: 72 percent / ammonia / methanol / 2 h / 20 °C

7.1: 63 percent / pyridine / 16 h / 25 °C

8.1: AgNO₃ / tetrahydrofuran / 0.5 h / 20 °C

8.2: 59 percent / pyridine / tetrahydrofuran / 12 h / 20 °C

With pyridine; ammonia; sodium methylate; tin(IV) chloride; silver nitrate; In tetrahydrofuran; 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-(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 (445417-53-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dioxane / 16 h / 35 - 40 °C

2.1: 75 percent / pyridine / 12 h / 35 - 40 °C

3.1: 72 percent / ammonia / methanol / 2 h / 20 °C

4.1: 63 percent / pyridine / 16 h / 25 °C

5.1: AgNO₃ / tetrahydrofuran / 0.5 h / 20 °C

5.2: 59 percent / pyridine / tetrahydrofuran / 12 h / 20 °C

With pyridine; ammonia; silver nitrate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol;

DOI:10.1021/jo025826t

upstream raw materials:

tert-butyldimethylsilyl chloride

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

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

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