Methanesulfonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Methanesulfonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 171563-34-1
• Molecular Formula: C₂₄H₃₃N₅O₆SSi
• Molecular Weight: 547.707
• Mol file: 171563-34-1.mol

Synonyms:Methanesulfonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Methanesulfonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester

There total 3 articles about Methanesulfonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl 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: 98.0%

methanesulfonyl chloride (124-63-0) + 6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (51549-40-7) → Methanesulfonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester (171563-34-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 0.25h;

DOI:10.1081/NCN-100105907

Reference yield:

5’-O-(4,4’dimethoxytrityl)-N6-(benzoyl)-3’-O-tert-butyldimethylsilyldeoxyadenosine (146578-12-3) → Methanesulfonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester (171563-34-1)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / chloroform / 0.5 h / 0 °C

2: pyridine / 3 h / 0 °C

With pyridine; toluene-4-sulfonic acid; In chloroform;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Methanesulfonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester (171563-34-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

2: toluene-4-sulfonic acid / chloroform / 0.5 h / 0 °C

3: pyridine / 3 h / 0 °C

With pyridine; 1H-imidazole; toluene-4-sulfonic acid; In chloroform; N,N-dimethyl-formamide;

upstream raw materials:

methanesulfonyl chloride

6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

5’-O-(4,4’dimethoxytrityl)-N6-(benzoyl)-3’-O-tert-butyldimethylsilyldeoxyadenosine

tert-butyldimethylsilyl chloride

Downstream raw materials:

5'-Azido-N₆-benzoyl-3'-O-t-butyldimethylsilyl-2',5'-dideoxyadenosine