2-amino-3-methyl-5-{2'-O-[2-(N,N-dibenzyl)aminoethyl]-β-D-ribofuranosyl}pyridine

Base Information

• Chemical Name: 2-amino-3-methyl-5-{2'-O-[2-(N,N-dibenzyl)aminoethyl]-β-D-ribofuranosyl}pyridine
• CAS No.: 1363735-85-6
• Molecular Formula: C₂₇H₃₃N₃O₄
• Molecular Weight: 463.577

Synonyms:2-amino-3-methyl-5-{2'-O-[2-(N,N-dibenzyl)aminoethyl]-β-D-ribofuranosyl}pyridine

Chemical Property of 2-amino-3-methyl-5-{2'-O-[2-(N,N-dibenzyl)aminoethyl]-β-D-ribofuranosyl}pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of 2-amino-3-methyl-5-{2'-O-[2-(N,N-dibenzyl)aminoethyl]-β-D-ribofuranosyl}pyridine

There total 12 articles about 2-amino-3-methyl-5-{2'-O-[2-(N,N-dibenzyl)aminoethyl]-β-D-ribofuranosyl}pyridine 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: 88.0%

2-amino-3-methyl-5-{2'-O-[2-(N,N-dibenzyl)aminoethyl]-3',5'-di-O-benzyl-β-D-ribofuranosyl}pyridine (1363735-83-4) → 2-amino-3-methyl-5-{2'-O-[2-(N,N-dibenzyl)aminoethyl]-β-D-ribofuranosyl}pyridine (1363735-85-6)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 ℃; for 7h; Inert atmosphere;

DOI:10.1002/chem.201102287

Reference yield:

(2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-ol (80795-53-5) → 2-amino-3-methyl-5-{2'-O-[2-(N,N-dibenzyl)aminoethyl]-β-D-ribofuranosyl}pyridine (1363735-85-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 h / -5 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4.1: hydrazine hydrate / ethanol / 24 h / 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 h / 0 °C / Inert atmosphere

6.1: sulfuric acid; acetic acid / water / 6 h / 80 °C / Inert atmosphere

7.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

8.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere

8.2: 6 h / -78 °C

9.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 26 h / -78 - 20 °C / Inert atmosphere

10.1: trifluoroacetic acid / 5 h / 20 °C / Inert atmosphere

11.1: boron trichloride / dichloromethane / 7 h / -78 °C / Inert atmosphere

With triethylsilane; lithium borohydride; n-butyllithium; tetrapropylammonium perruthennate; sulfuric acid; boron trifluoride diethyl etherate; boron trichloride; sodium hydride; hydrazine hydrate; acetic acid; 4-methylmorpholine N-oxide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 3.1: Mitsunobu reaction;

DOI:10.1002/chem.201102287

Reference yield:

methyl 2-O-(2-aminoethyl)-3,5-di-O-benzyl-α-D-ribofuranoside (1363735-70-9) → 2-amino-3-methyl-5-{2'-O-[2-(N,N-dibenzyl)aminoethyl]-β-D-ribofuranosyl}pyridine (1363735-85-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 h / 0 °C / Inert atmosphere

2.1: sulfuric acid; acetic acid / water / 6 h / 80 °C / Inert atmosphere

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

4.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere

4.2: 6 h / -78 °C

5.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 26 h / -78 - 20 °C / Inert atmosphere

6.1: trifluoroacetic acid / 5 h / 20 °C / Inert atmosphere

7.1: boron trichloride / dichloromethane / 7 h / -78 °C / Inert atmosphere

With triethylsilane; n-butyllithium; tetrapropylammonium perruthennate; sulfuric acid; boron trifluoride diethyl etherate; boron trichloride; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/chem.201102287

upstream raw materials:

(2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-ol

methyl 2-O-(2-aminoethyl)-3,5-di-O-benzyl-α-D-ribofuranoside

methyl 2-O-[2-(N,N-dibenzyl)aminoethyl]-3,5-di-O-benzyl-α-D-ribofuranoside

2-O-[2-(N,N-dibenzyl)aminoethyl]-3,5-di-O-benzyl-D-ribolactone

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