Guanosine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[1-(2-cyanoethoxy)ethyl]- N-(phenoxyacetyl)-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]

Base Information

• Chemical Name: Guanosine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[1-(2-cyanoethoxy)ethyl]- N-(phenoxyacetyl)-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]
• CAS No.: 828247-89-8
• Molecular Formula: C53H61N8O11P
• Molecular Weight: 1017.09

Synonyms:

Chemical Property of Guanosine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[1-(2-cyanoethoxy)ethyl]- N-(phenoxyacetyl)-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Guanosine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[1-(2-cyanoethoxy)ethyl]- N-(phenoxyacetyl)-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]

There total 5 articles about Guanosine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[1-(2-cyanoethoxy)ethyl]- N-(phenoxyacetyl)-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite] 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: 68.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-[1-(2-cyano-ethoxy)-ethoxy]-4-hydroxy-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenoxy-acetamide (828247-78-5) → Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[1-(2-cyano-ethoxy)-ethoxy]-5-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (828247-89-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/j.tetlet.2004.10.151

Reference yield:

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[1-(2-cyano-ethoxy)-ethoxy]-5-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (828247-89-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydrogen sulfate

2.1: 75 percent / pyridinium p-toluenesulfonate / dioxane / 55 °C

3.1: tetrabutylammonium fluoride; acetic acid / tetrahydrofuran

3.2: 93 percent / pyridine

4.1: 68 percent / diisopropylethylamine / CH₂Cl₂

With sodium hydrogen sulfate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1016/j.tetlet.2004.10.151

Reference yield:

N-(9-{(2R,3R,3aR,9aR)-3-[1-(2-Cyano-ethoxy)-ethoxy]-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenoxy-acetamide (828247-68-3) → Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[1-(2-cyano-ethoxy)-ethoxy]-5-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (828247-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutylammonium fluoride; acetic acid / tetrahydrofuran

1.2: 93 percent / pyridine

2.1: 68 percent / diisopropylethylamine / CH₂Cl₂

With tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2004.10.151

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-[1-(2-cyano-ethoxy)-ethoxy]-4-hydroxy-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenoxy-acetamide

vinyloxypropionitrile

1,2-bis-(2-cyanoethoxy)ethane

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