tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-(cyclopentylamino)-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate

Base Information

• Chemical Name: tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-(cyclopentylamino)-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate
• CAS No.: 1449781-85-4
• Molecular Formula: C₃₆H₅₆N₆O₃Si
• Molecular Weight: 648.965

Synonyms:tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-(cyclopentylamino)-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate

Chemical Property of tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-(cyclopentylamino)-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate

Chemical Property:

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Technology Process of tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-(cyclopentylamino)-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate

There total 7 articles about tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-(cyclopentylamino)-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate 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: 81.0%

tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-chloro-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate (1449781-84-3) + Cyclopentamine (1003-03-8) → tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-(cyclopentylamino)-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate (1449781-85-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 135 ℃; for 0.5h; Sealed tube; Microwave irradiation;

DOI:10.1016/j.bmc.2013.04.080

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-(cyclopentylamino)-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate (1449781-85-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap / dimethyl sulfoxide / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere

3.1: triphenylphosphine / tetrahydrofuran / 0.03 h / 20 °C / Inert atmosphere

3.2: 0.25 h / 20 °C / Inert atmosphere

4.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

4.2: 20 - 40 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 0.5 h / 135 °C / Sealed tube; Microwave irradiation

With dmap; sodium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; 3.1: |Mitsunobu Displacement / 3.2: |Mitsunobu Displacement / 4.1: |Mitsunobu Displacement / 4.2: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2013.04.080

Reference yield:

tert-butyl (2-amino-6-chloro-9H-purin-9-yl)carboxylate (442685-41-8) → tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-(cyclopentylamino)-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate (1449781-85-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere

2.1: triphenylphosphine / tetrahydrofuran / 0.03 h / 20 °C / Inert atmosphere

2.2: 0.25 h / 20 °C / Inert atmosphere

3.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

3.2: 20 - 40 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 0.5 h / 135 °C / Sealed tube; Microwave irradiation

With sodium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; 2.1: |Mitsunobu Displacement / 2.2: |Mitsunobu Displacement / 3.1: |Mitsunobu Displacement / 3.2: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2013.04.080

upstream raw materials:

di-tert-butyl dicarbonate

tert-butyl (2-amino-6-chloro-9H-purin-9-yl)carboxylate

tert-butyl {9-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-chloro-9H-purin-2-yl}(4-cyclohexylbenzyl)carbamate

Cyclopentamine

Downstream raw materials:

tert-butyl (4-cyclohexylbenzyl)[6-(cyclopentylamino)-9-(2-hydroxyethyl)-9H-purin-2-yl]carbamate

2-{2-[(4-cyclohexylbenzyl)amino]-6-(cyclopentylamino)-9H-purin-9-yl}ethyl sulfamate

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