Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate)

Base Information

• Chemical Name: Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate)
• CAS No.: 93134-41-9
• Molecular Formula: C19H25N5O7
• Molecular Weight: 435.43100
• Mol file: 93134-41-9.mol

Synonyms:N-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine;3'-O-Levulinyl--N2-isobutyryl-2'-deoxyguanosine;4-Oxo-pentanoic acid (2R,3S,5R)-2-hydroxymethyl-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester;5'-OH-dGi-Bu-3'-O-Lev;3'-O-Levulinyl-N2-isobutyryl-2'-deoxyguanosine;

Chemical Property of Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate)

Chemical Property:

• PSA: 165.50000
• Density: 1.56±0.1 g/cm3(Predicted)
• LogP: 0.34790

Purity/Quality:

97% ^*data from raw suppliers

3''-O-Levulinoyl-N-benzoyl-2''-deoxyguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3''-O-Levulinoyl-N-benzoyl-2''-deoxyguanosine is a protected nucleotide derivative/building block.

Technology Process of Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate)

There total 10 articles about Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate) 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: 76.0%

N-isobutyryl-3',5'-di-O-levulinyl-2'-deoxyguanosine (440327-43-5) → N-isobutyryl-2'-deoxyguanosine (68892-42-2) + N2-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine (93134-41-9)

Guidance literature:

With Candida antarctica lipase B; phosphate buffer; In 1,4-dioxane; at 40 ℃; for 14h; pH=7;

DOI:10.1021/jo020080k

Reference yield:

5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine (68892-41-1) → N2-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine (93134-41-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,3-dicyclohexylcarbodiimide; (N,N-dimethylamino)pyridine / dioxane / 3 h / 25 °C

2: acetic acid / 2 h / 25 °C

With dmap; acetic acid; dicyclohexyl-carbodiimide; In 1,4-dioxane;

DOI:10.1021/ja048377i

Reference yield:

levulinic acid (123-76-2) → N2-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine (93134-41-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,3-dicyclohexylcarbodiimide; (N,N-dimethylamino)pyridine / dioxane / 3 h / 25 °C

2: acetic acid / 2 h / 25 °C

With dmap; acetic acid; dicyclohexyl-carbodiimide; In 1,4-dioxane;

DOI:10.1021/ja048377i

upstream raw materials:

4-Oxo-pentanoic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

N-isobutyryl-3',5'-di-O-levulinyl-2'-deoxyguanosine

N-isobutyryl-2'-deoxyguanosine

O-levulinyl acetonoxime

Downstream raw materials:

4-Oxo-pentanoic acid (2R,3S,5R)-2-[diisopropylamino-(4-nitro-phenoxy)-phosphanyloxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

C₅₇H₆₄N₁₁O₁₅P

C₅₃H₅₉N₈O₁₅P

N₂-isobutyryl-3'-O-(2-cyanoethyl)-phosphonate-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine

Refernces

• 1、 Marchan, Vicente,Cieslak, Jacek,Livengood, Victor,Beaucage, Serge L.. "2,2,5,5-Tetramethylpyrrolidin-3-one-1-sulfinyl group for 5′-hydroxyl protection of deoxyribonucleoside phosphoramidites in the solid-phase preparation of DNA oligonucleotides". . p. 9601 - 9610. Retrieved 2007/10/03.
• 2、 Garcia, Javier,Fernandez, Susana,Ferrero, Miguel,Sanghvi, Yogesh S.,Gotor, Vicente. "Building blocks for the solution phase synthesis of oligonucleotides: Regioselective hydrolysis of 3′,5′-di-O-levulinylnucleosides using an enzymatic approach". . p. 4513 - 4519. Retrieved 2007/10/03.