N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

Base Information

• Chemical Name: N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]
• CAS No.: 439097-95-7
• Molecular Formula: C₄₃H₅₀N₇O₁₀P
• Molecular Weight: 855.885

Synonyms:N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

Chemical Property of N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

Chemical Property:

Purity/Quality:

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Technology Process of N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

There total 9 articles about N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate] 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: 66.0%

N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine (439097-93-5) + C31H40N3O2P (660851-59-2) → N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate] (439097-95-7)

Guidance literature:

N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine; C₃₁H₄₀N₃O₂P; With 1-methyl-5-mercaptotetrazole; In acetonitrile; at 20 ℃; for 1h;

With tert.-butylhydroperoxide; In decane; acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.1021/jo0351466

Reference yield: 27.0%

(S)-(-)-1-trityl-2-pyrrolidinecarboxamide (82935-40-8) + N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-(methyl N,N-diisopropylphosphoramidite) (439097-94-6) → N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate] (439097-95-7)

Guidance literature:

(S)-(-)-1-trityl-2-pyrrolidinecarboxamide; N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-(methyl N,N-diisopropylphosphoramidite); With 5-(3,5-dinitrophenyl)-1H-tetrazole; In dichloromethane; acetonitrile; at 20 ℃; for 0.166667h;

With tert.-butylhydroperoxide; In dichloromethane; acetonitrile; at 20 ℃; for 0.0833333h;

With iodine; In pyridine; water; at 20 ℃; for 0.5h; Further stages.;

DOI:10.1021/jo016176g

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate] (439097-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 5.58 g / triethylamine / methanol / 2 h / 20 °C

2.1: 5-mercapto-1-methyl-1H-tetrazole / acetonitrile / 1 h / 20 °C

2.2: 66 percent / tert-butyl hydroperoxide / acetonitrile; decane / 0.17 h / 20 °C

With triethylamine; 1-methyl-5-mercaptotetrazole; In methanol; acetonitrile;

DOI:10.1021/jo0351466

upstream raw materials:

(S)-(-)-1-trityl-2-pyrrolidinecarboxamide

N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-(methyl N,N-diisopropylphosphoramidite)

N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine

C₃₁H₄₀N₃O₂P

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