S-{N₆-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-N-Fmoc-L-cysteine methyl ester

Base Information

• Chemical Name: S-{N₆-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-N-Fmoc-L-cysteine methyl ester
• CAS No.: 1275513-35-3
• Molecular Formula: C₃₉H₄₀N₆O₈S
• Molecular Weight: 752.848

Synonyms:S-{N₆-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-N-Fmoc-L-cysteine methyl ester

Chemical Property of S-{N₆-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-N-Fmoc-L-cysteine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of S-{N₆-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-N-Fmoc-L-cysteine methyl ester

There total 3 articles about S-{N₆-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-N-Fmoc-L-cysteine methyl ester 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: 94.0%

tert-butyl N6-(benzyloxycarbonyl)-8-(chloromethyl)adenine-9-aceta (1275513-51-3) + 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-mercaptopropionic acid methyl ester (233266-69-8) → S-{N6-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-N-Fmoc-L-cysteine methyl ester (1275513-35-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/ja200829s

Reference yield:

tert-butyl N4-[(benzyloxy)carbonyl]-8-(hydroxymethyl)adenine-9-acetate (1182206-90-1) → S-{N6-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-N-Fmoc-L-cysteine methyl ester (1275513-35-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: lithium chloride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 h / 20 °C / Inert atmosphere

With N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja200829s

Reference yield:

C21H25N5O7S → S-{N6-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-N-Fmoc-L-cysteine methyl ester (1275513-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium chloride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 h / 20 °C / Inert atmosphere

With N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja200829s

upstream raw materials:

tert-butyl N₄-[(benzyloxy)carbonyl]-8-(hydroxymethyl)adenine-9-acetate

tert-butyl N₆-(benzyloxycarbonyl)-8-(chloromethyl)adenine-9-aceta

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-mercaptopropionic acid methyl ester

Downstream raw materials:

S-[N₆-(benzyloxycarbonyl)-9-(carboxymethyl)adenine-8-methyl]-N-Fmoc-L-cysteine methyl ester

S-[N₆-(benzyloxycarbonyl)-9-(carboxymethyl)adenine-8-methyl]-L-cysteine methyl ester

{S-[N6-(benzyloxycarbonyl)-9-(ω-carbonylmethyl)adenine-8-methyl]-N-Fmoc-L-cysteine methyl ester}-S-{N6-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-L-cysteine

{S-[N6-(benzyloxycarbonyl)-9-(ω-carbonylmethyl)adenine-8-methyl]-L-cysteine methyl ester}-S-{N6-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-L-cysteine

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