N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-β-D-ribo-hept-5-enofuranosyl]adenine

Base Information

Chemical Name:N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-β-D-ribo-hept-5-enofuranosyl]adenine
CAS No.:1312944-75-4
Molecular Formula:C₂₀H₂₁N₇O₈
Molecular Weight:487.429
Hs Code.:

Synonyms:N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-β-D-ribo-hept-5-enofuranosyl]adenine

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Chemical Property of N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-β-D-ribo-hept-5-enofuranosyl]adenine

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Technology Process of N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-β-D-ribo-hept-5-enofuranosyl]adenine

There total 10 articles about N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-β-D-ribo-hept-5-enofuranosyl]adenine 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: 58.0%

: 1312944-66-3
N6-methyl-9-{(5E)-5,6,7-trideoxy-7-[6-nitro-2,2-bis(4-methoxyphenyl)-1,3-benzodioxole-4-carboxamido]-β-D-ribo-hept-5-enofuranosyl}adenine

: 1312944-75-4
N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-β-D-ribo-hept-5-enofuranosyl]adenine

Guidance literature:: With trifluoroacetic acid; In water; at 0 ℃; for 0.25h; Inert atmosphere;
DOI:10.1002/chem.201003648

Reference yield:

: 1204745-03-8
(E)-1,2,3-tri-O-acetyl-5,6,7-trideoxy-7-C-phthalimido-D-ribohept-5-enofuranose

: 1312944-75-4
N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-β-D-ribo-hept-5-enofuranosyl]adenine

Guidance literature:: Multi-step reaction with 4 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C / Inert atmosphere

1.2: 20 h / 60 °C / Inert atmosphere

2.1: methylamine / ethanol / 60 h / 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

3.2: 5 h / 0 °C / Inert atmosphere

4.1: trifluoroacetic acid / water / 0.25 h / 0 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; N-ethyl-N,N-diisopropylamine; HATU; methylamine; trifluoroacetic acid; In ethanol; water; N,N-dimethyl-formamide; toluene; 1.2: Vorbruggen nucleosidation reaction;
DOI:10.1002/chem.201003648

Reference yield:

: 888956-31-8
methyl 2,2-bis(4-methoxyphenyl)-6-nitro-1,3-benzodioxole-4-carboxylate

: 1312944-75-4
N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-β-D-ribo-hept-5-enofuranosyl]adenine

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate / tetrahydrofuran / 3 h / 70 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

2.2: 5 h / 0 °C / Inert atmosphere

3.1: trifluoroacetic acid / water / 0.25 h / 0 °C / Inert atmosphere

With lithium hydroxide monohydrate; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1002/chem.201003648