N⁶-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine

Base Information

• Chemical Name: N⁶-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine
• CAS No.: 185628-20-0
• Molecular Formula: C₄₁H₄₉N₅O₈Si
• Molecular Weight: 767.954

Synonyms:N⁶-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine

Chemical Property of N⁶-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of N⁶-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine

There total 5 articles about N⁶-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine 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: 45.0%

tert-butyldimethylsilyl chloride (18162-48-6) + N6-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)adenosine (210684-26-7) → N6-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)adenosine (210684-28-9) + N6-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine (185628-20-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1055/s-1998-1822

Reference yield:

O2',O3',O5'-tris-trimethylsilanyl-adenosine (10457-15-5) → N6-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine (185628-20-0)

Guidance literature:

Multi-step reaction with 4 steps

1: N-methylimidazole / CH₂Cl₂

2: 17.5 g / Et₃N / methanol / 12 h

3: 77 percent / pyridine; dimethylformamide / 0 - 20 °C

4: 33 percent / imidazole / dimethylformamide

With 1H-imidazole; 1-methyl-1H-imidazole; triethylamine; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: desilylation / 3: Etherification / 4: silylation;

DOI:10.1080/07328319908044842

Reference yield:

[9-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-carbamic acid allyl ester → N6-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine (185628-20-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 17.5 g / Et₃N / methanol / 12 h

2: 77 percent / pyridine; dimethylformamide / 0 - 20 °C

3: 33 percent / imidazole / dimethylformamide

With 1H-imidazole; triethylamine; In pyridine; methanol; N,N-dimethyl-formamide; 1: desilylation / 2: Etherification / 3: silylation;

DOI:10.1080/07328319908044842

upstream raw materials:

tert-butyldimethylsilyl chloride

N⁶-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)adenosine

O^2'_,O3'_,O5'-tris-trimethylsilanyl-adenosine

N⁶-[(allyloxy)carbonyl]adenosine

Downstream raw materials:

N⁶-[(allyloxy)carbonyl]-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)adenosine 3'-(allyl N,N'-diisopropylphosphoramidite)

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