N-[9-(6-Hydroxymethyl-4-trityl-morpholin-2-yl)-9H-purin-6-yl]-benzamide

Base Information

• Chemical Name: N-[9-(6-Hydroxymethyl-4-trityl-morpholin-2-yl)-9H-purin-6-yl]-benzamide
• CAS No.: 956139-16-5
• Molecular Formula: C36H32N6O3
• Molecular Weight: 596.688
• European Community (EC) Number: 811-516-8
• Mol file: 956139-16-5.mol

Synonyms:956139-16-5;N-[9-(6-Hydroxymethyl-4-trityl-morpholin-2-yl)-9H-purin-6-yl]-benzamide;N6-Benzoyl-7'-OH-N-trityl morpholino adenosine;N-(9-((2R,6S)-6-(Hydroxymethyl)-4-tritylmorpholin-2-yl)-9H-purin-6-yl)benzamide;N-[9-[(2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl]purin-6-yl]benzamide;N6-Benzoyl-7 inverted exclamation mark -OH-N-trityl morpholino adenine;SCHEMBL16207829;MFCD22666304;HY-W357200;WS-02647;CS-0468396;F14251;A857338

Chemical Property of N-[9-(6-Hydroxymethyl-4-trityl-morpholin-2-yl)-9H-purin-6-yl]-benzamide

Chemical Property:

• Melting Point: 172 - 174 °C
• PSA: 105.40000
• LogP: 5.27330
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 596.25358890
• Heavy Atom Count: 45
• Complexity: 900

Purity/Quality:

97% ^*data from raw suppliers

N6-Benzoyl-7'-hydroxy-N-trityl morpholino adenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(OC(CN1C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)N5C=NC6=C(N=CN=C65)NC(=O)C7=CC=CC=C7)CO
• Isomeric SMILES: C1[C@H](O[C@H](CN1C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)N5C=NC6=C(N=CN=C65)NC(=O)C7=CC=CC=C7)CO

Technology Process of N-[9-(6-Hydroxymethyl-4-trityl-morpholin-2-yl)-9H-purin-6-yl]-benzamide

There total 11 articles about N-[9-(6-Hydroxymethyl-4-trityl-morpholin-2-yl)-9H-purin-6-yl]-benzamide 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: 96.0%

(2′R,6′S)-N6-benzoyl-9-{6′-[(tert-butyldiphenylsilyloxy)methyl]-N-tritylmorpholin-2′-yl}adenine (1415645-67-8) → (2′R,6′S)-N6-benzoyl-9-[6′-(hydroxymethyl)-N-tritylmorpholin-2′-yl]adenine (956139-16-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b00719

Reference yield:

7-O-(tert-butyldiphenylsilyl)-N-trityl morpholinoadenosine (1415645-57-6) → (2′R,6′S)-N6-benzoyl-9-[6′-(hydroxymethyl)-N-tritylmorpholin-2′-yl]adenine (956139-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 18 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine;

DOI:10.1080/15257770.2012.724491

Reference yield:

7-O-(tert-butyldiphenylsilyl)morpholinoadenosine (1415645-51-0) → (2′R,6′S)-N6-benzoyl-9-[6′-(hydroxymethyl)-N-tritylmorpholin-2′-yl]adenine (956139-16-5)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Molecular sieve; Inert atmosphere

2: pyridine / 18 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

With tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;

DOI:10.1080/15257770.2012.724491

upstream raw materials:

7-O-(tert-butyldiphenylsilyl)morpholinoadenosine

7-O-(tert-butyldiphenylsilyl)-N-trityl morpholinoadenosine

(2′R,6′S)-N⁶-benzoyl-9-{6′-[(tert-butyldiphenylsilyloxy)methyl]-N-tritylmorpholin-2′-yl}adenine

G

Downstream raw materials:

phosphoramidochloridic acid, N,N-dimethyl-, [6-[6-(benzoylamino)-9H-purin-9-yl]-4-(triphenylmethyl)-2-morpholinyl]methyl ester