6-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-6-thioinosine

Base Information

• Chemical Name: 6-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-6-thioinosine
• CAS No.: 293300-96-6
• Molecular Formula: C₃₄H₃₃N₅O₆S
• Molecular Weight: 639.732
• Mol file: 293300-96-6.mol

Synonyms:6-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-6-thioinosine

Chemical Property of 6-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-6-thioinosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-6-thioinosine

There total 4 articles about 6-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-6-thioinosine 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: 96.0%

3-mercaptopropionitrile (1001-58-7) + (2R,3S,4R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diol (97695-14-2) → 6-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-6-thioinosine (293300-96-6)

Guidance literature:

With 1-Methylpyrrolidine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo991432z

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 6-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-6-thioinosine (293300-96-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / 6 h / 20 °C

2: 96 percent / N-methylpyrrolidine / CH₂Cl₂ / 2 h / 20 °C

With 1-Methylpyrrolidine; In pyridine; dichloromethane; 1: Alkylation / 2: Substitution;

DOI:10.1021/jo991432z

Reference yield:

6-Chloropurine riboside (2004-06-0) → 6-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-6-thioinosine (293300-96-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / 6 h / 20 °C

2: 96 percent / N-methylpyrrolidine / CH₂Cl₂ / 2 h / 20 °C

With 1-Methylpyrrolidine; In pyridine; dichloromethane; 1: Alkylation / 2: Substitution;

DOI:10.1021/jo991432z

upstream raw materials:

4,4'-dimethoxytrityl chloride

3-mercaptopropionitrile

(2R,3S,4R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diol

6-Chloropurine riboside

Downstream raw materials:

Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2-cyano-ethylsulfanyl)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-6-thioinosine

Refernces

• 1、 Adams, Chris J.,Farrow, Mark A.,Murray, James B.,Kelly, Sharon M.,Price, Nicholas C.,Stockley, Peter G.. "Incorporation of 6-thioinosine into oligoribonucleotides". . p. 4637 - 4640. Retrieved 2007/10/02.