O⁶-allyl-N²-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine 3'-(allyl N,N'-diisorpopylphosphoramidite)

Base Information

• Chemical Name: O⁶-allyl-N²-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine 3'-(allyl N,N'-diisorpopylphosphoramidite)
• CAS No.: 243844-65-7
• Molecular Formula: C₅₃H₇₁N₆O₁₀PSi
• Molecular Weight: 1011.24

Synonyms:O⁶-allyl-N²-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine 3'-(allyl N,N'-diisorpopylphosphoramidite)

Chemical Property of O⁶-allyl-N²-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine 3'-(allyl N,N'-diisorpopylphosphoramidite)

Chemical Property:

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Technology Process of O⁶-allyl-N²-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine 3'-(allyl N,N'-diisorpopylphosphoramidite)

There total 7 articles about O⁶-allyl-N²-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine 3'-(allyl N,N'-diisorpopylphosphoramidite) 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: 72.0%

(allyloxy)bis(diisopropylamino)phosphine (108554-72-9) + O6-allyl-N2-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine (243844-62-4) → O6-allyl-N2-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine 3'-(allyl N,N'-diisorpopylphosphoramidite) (243844-65-7)

Guidance literature:

With N,N-diisopropylamine tetrazolide; In acetonitrile; for 12h;

DOI:10.1080/07328319908044842

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → O6-allyl-N2-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine 3'-(allyl N,N'-diisorpopylphosphoramidite) (243844-65-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / pyridine; dimethylformamide / 1.5 h / 55 °C

2: 29 percent / imidazole / dimethylformamide / 1 h / 60 °C

3: 72 percent / diisopropylammonium tetrazolide / acetonitrile / 12 h

With 1H-imidazole; N,N-diisopropylamine tetrazolide; In pyridine; N,N-dimethyl-formamide; acetonitrile; 1: Etherification / 2: silylation / 3: Esterification;

DOI:10.1080/07328319908044842

Reference yield:

2',3',5'-tri-O-acetyl-guanosine (6979-94-8) → O6-allyl-N2-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine 3'-(allyl N,N'-diisorpopylphosphoramidite) (243844-65-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / Ph₃P; diethyl azodicarboxylate / dioxane / 3 h / 60 °C

2: 66 percent / tert-butylmagnesium chloride / tetrahydrofuran / 1 h

3: 2.55 g / NaOH / aq. ethanol / 0.5 h

4: 77 percent / pyridine; dimethylformamide / 1.5 h / 55 °C

5: 29 percent / imidazole / dimethylformamide / 1 h / 60 °C

6: 72 percent / diisopropylammonium tetrazolide / acetonitrile / 12 h

With 1H-imidazole; sodium hydroxide; tert-butylmagnesium chloride; N,N-diisopropylamine tetrazolide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; N,N-dimethyl-formamide; acetonitrile; 1: Acylation / 2: Acylation / 3: Deacetylation / 4: Etherification / 5: silylation / 6: Esterification;

DOI:10.1080/07328319908044842

upstream raw materials:

(allyloxy)bis(diisopropylamino)phosphine

O⁶-allyl-N²-[(allyloxy)carbonyl]-5'-O-(p,p'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)guanosine

4,4'-dimethoxytrityl chloride

2',3',5'-tri-O-acetyl-guanosine

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