N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine

Base Information

• Chemical Name: N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine
• CAS No.: 1447827-90-8
• Molecular Formula: C₄₈H₅₄N₆O₈SeSi
• Molecular Weight: 950.038

Synonyms:N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine

Chemical Property of N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine

Chemical Property:

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Technology Process of N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine

There total 2 articles about N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine 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:

Se-(2-cyanoethyl) diselenide (910318-61-5) + N2-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2,4,6-triisopropylbenzenesulfonyl)guanosine → N2-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine (1447827-90-8)

Guidance literature:

Se-(2-cyanoethyl) diselenide; N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2,4,6-triisopropylbenzenesulfonyl)guanosine; With boric acid; In ethanol; at 0 ℃; for 0.0833333h; Inert atmosphere;

With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; for 0.0833333h; pH=< 8; Inert atmosphere;

DOI:10.1021/ol401698n

Reference yield:

5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N2-phenoxyacetylguanosine (121058-84-2) → N2-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine (1447827-90-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; dmap / dichloromethane / 0.17 h / 20 °C

2.1: boric acid / ethanol / 0.08 h / 0 °C / Inert atmosphere

2.2: 0.08 h / 0 - 20 °C / pH < 8 / Inert atmosphere

With dmap; boric acid; triethylamine; In ethanol; dichloromethane;

DOI:10.1021/ol401698n

Reference yield: 78.0%

N2-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine (1447827-90-8) + chloro-(2-cyanoethyl)-diisopropylaminophosphane (132133-40-5) → N2-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine 3′-(2-cyanoethyl)-N,N-diisopropyl phosphoramidite (1447827-91-9,1447827-92-0)

Guidance literature:

N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine; With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.166667h; Inert atmosphere;

chloro-(2-cyanoethyl)-diisopropylaminophosphane; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol401698n

upstream raw materials:

5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N2-phenoxyacetylguanosine

Se-(2-cyanoethyl) diselenide

Downstream raw materials:

N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine 3′-(2-cyanoethyl)-N,N-diisopropyl phosphoramidite

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