tert-butyl 9-((1S,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopentyl)-6-iodo-9H-purin-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl 9-((1S,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopentyl)-6-iodo-9H-purin-2-ylcarbamate
• CAS No.: 1328921-87-4
• Molecular Formula: C₃₃H₃₈IN₅O₆
• Molecular Weight: 727.599

Synonyms:tert-butyl 9-((1S,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopentyl)-6-iodo-9H-purin-2-ylcarbamate

Chemical Property of tert-butyl 9-((1S,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopentyl)-6-iodo-9H-purin-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 9-((1S,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopentyl)-6-iodo-9H-purin-2-ylcarbamate

There total 12 articles about tert-butyl 9-((1S,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopentyl)-6-iodo-9H-purin-2-ylcarbamate 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: 70.0%

(1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol (1328921-71-6) + N2-Boc-6-iodopurine → tert-butyl 9-((1S,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopentyl)-6-iodo-9H-purin-2-ylcarbamate (1328921-87-4)

Guidance literature:

(1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol; N₂-Boc-6-iodopurine; With triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 0.5h;

With diethylazodicarboxylate; In tetrahydrofuran;

Reference yield:

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one (76704-05-7) → tert-butyl 9-((1S,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopentyl)-6-iodo-9H-purin-2-ylcarbamate (1328921-87-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / 2 h / 20 °C

2.1: diisobutylaluminium hydride / toluene / 1 h / -78 - -60 °C / Inert atmosphere

2.2: 1.5 h / 0 °C

3.1: palladium diacetate; copper diacetate / 8 h / 20 °C / Reflux

4.1: sodium hydroxide; methanol / 1 h / 20 °C

5.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 0 °C

With methanol; diisobutylaluminium hydride; toluene-4-sulfonic acid; triphenylphosphine; sodium hydroxide; copper diacetate; palladium diacetate; In tetrahydrofuran; toluene; 5.1: Mitsunobu reaction;

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → tert-butyl 9-((1S,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopentyl)-6-iodo-9H-purin-2-ylcarbamate (1328921-87-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane

1.2: 20 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / Inert atmosphere

2.2: 2 h / 0 °C

3.1: triethylamine / tetrahydrofuran / 0.5 h / -70 - 60 °C

3.2: 2 h / -70 - 60 °C / Reflux

4.1: sodium hydrogencarbonate; ozone / dichloromethane; methanol / -78 - 60 °C

4.2: 0.17 h / -78 °C

5.1: pyridine / dichloromethane / 0.5 h / 50 °C

5.2: 1 h / 0 - 20 °C

5.3: 0 - 10 °C

6.1: dmap / dichloromethane / 0.5 h / 0 - 10 °C

6.2: 2 h / 20 °C

7.1: lithium iodide / N,N-dimethyl acetamide / 1.5 h / 20 - 100 °C

7.2: 16 h / 90 - 100 °C

8.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium iodide; dmap; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide; 8.1: Mitsunobu reaction;

upstream raw materials:

Benzyloxymethyl chloride

(3aS,4R,5S,6aR)-hexahydro-5-(methoxymethoxy)-4-((methoxymethoxy)methyl)cyclopenta[b]furan-2-one

(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-hexahydrocyclo pentafuran-2-one

(3aS,4R,5S,6aR)-hexahydro-5-(methoxymethoxy)-4-((methoxymethoxy)methyl)-2H-cyclopenta[b]furan-2-ol

Downstream raw materials:

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