N-[9-((1R,3R,4S)-3-{[(dimethoxytrityl)oxy]methyl}-4-hydroxycyclopentyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-acetamide

Base Information

• Chemical Name: N-[9-((1R,3R,4S)-3-{[(dimethoxytrityl)oxy]methyl}-4-hydroxycyclopentyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-acetamide
• CAS No.: 874486-36-9
• Molecular Formula: C₃₄H₃₅N₅O₆
• Molecular Weight: 609.682
• Mol file: 874486-36-9.mol

Synonyms:N-[9-((1R,3R,4S)-3-{[(dimethoxytrityl)oxy]methyl}-4-hydroxycyclopentyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-acetamide

Chemical Property of N-[9-((1R,3R,4S)-3-{[(dimethoxytrityl)oxy]methyl}-4-hydroxycyclopentyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[9-((1R,3R,4S)-3-{[(dimethoxytrityl)oxy]methyl}-4-hydroxycyclopentyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-acetamide

There total 13 articles about N-[9-((1R,3R,4S)-3-{[(dimethoxytrityl)oxy]methyl}-4-hydroxycyclopentyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-acetamide 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: 60.0%

N-{9-[(1R,3S,4R)-3-hydroxy-4-hydroxymethyl-cyclopentyl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-acetamide (874486-35-8) + 4,4'-dimethoxytrityl chloride (40615-36-9) → N-[9-((1R,3R,4S)-3-{[(dimethoxytrityl)oxy]methyl}-4-hydroxycyclopentyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-acetamide (874486-36-9)

Guidance literature:

With pyridine; for 2.5h;

DOI:10.1021/ja0549188

Reference yield:

tert-butyl-N-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]carbamate (153045-91-1) → N-[9-((1R,3R,4S)-3-{[(dimethoxytrityl)oxy]methyl}-4-hydroxycyclopentyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-acetamide (874486-36-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / H₂O / Heating

2: 86 percent / diisopropylethylamine / dimethylformamide / 3 h / 0 - 75 °C

3: 79 percent / imidazole / dimethylformamide / 3 h / 20 °C

4: H₂ / Pd/C / ethanol / 900.07 Torr

5: 75.3 mg / 20 - 100 °C

6: 85 percent / pyridine*HF / ethyl acetate / 20 °C

7: 60 percent / pyridine / 2.5 h

With pyridine; 1H-imidazole; water; hydrogen; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja0549188

Reference yield:

tert-butyl N-{(1S,2R,4R,5R)-4-[(tert-butyldimethylsilyloxy)methyl]-6-oxa-bicyclo[3.1.0]hex-2-yl}-carbamate (874486-39-2) → N-[9-((1R,3R,4S)-3-{[(dimethoxytrityl)oxy]methyl}-4-hydroxycyclopentyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-acetamide (874486-36-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / Red-Al(R) / toluene / 1 h / 20 °C

2: 100 percent / H₂O / Heating

3: 86 percent / diisopropylethylamine / dimethylformamide / 3 h / 0 - 75 °C

4: 79 percent / imidazole / dimethylformamide / 3 h / 20 °C

5: H₂ / Pd/C / ethanol / 900.07 Torr

6: 75.3 mg / 20 - 100 °C

7: 85 percent / pyridine*HF / ethyl acetate / 20 °C

8: 60 percent / pyridine / 2.5 h

With pyridine; 1H-imidazole; water; hydrogen; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0549188

upstream raw materials:

N-{9-[(1R,3S,4R)-3-hydroxy-4-hydroxymethyl-cyclopentyl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-acetamide

4,4'-dimethoxytrityl chloride

N-{9-[(1R,3S,4R)-3-[(tert-butyldimethylsilyl)oxy]-4-{[(tert-butyldimethylsilyl)oxy]methyl}cyclopentyl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-acetamide

(+)-(1S, 2R, 4R)-4-amino-2-(hydroxymethyl)-1-cyclopentanol