3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Base Information

• Chemical Name: 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine
• CAS No.: 312709-86-7
• Molecular Formula: C₄₃H₅₅N₅O₈Si
• Molecular Weight: 798.024
• Mol file: 312709-86-7.mol

Synonyms:3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Chemical Property of 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

There total 2 articles about 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}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: 88.0%

acetic anhydride (108-24-7) + (2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-triisopropylsilanyloxymethoxy-tetrahydro-furan-3-ol (872548-42-0) → 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (312709-86-7)

Guidance literature:

With dmap; In pyridine; at 20 ℃; for 0.5h;

DOI:10.1002/hlca.200590209

Reference yield:

N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (253586-22-0) → 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (312709-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1: MeNH₂ / ethanol / 0.5 h / 20 °C

2: DMAP / pyridine / 0.5 h / 20 °C

With dmap; methylamine; In pyridine; ethanol; 1: Deacetylation / 2: Acetylation;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

Reference yield:

phosgene (75-44-5) + 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (312709-86-7) → C44H54ClN5O9Si

Guidance literature:

With dmap; In pyridine; dichloromethane; toluene; at 20 ℃; for 0.25h;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

upstream raw materials:

acetic anhydride

(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-triisopropylsilanyloxymethoxy-tetrahydro-furan-3-ol

N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-N⁶-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyloxy)methyl]adenosine}

5'-O-(4,4'-dimethoxytrityl)-N⁶-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine 3'-(2-cyanoethyl diisopropylphosphoramidite)