N(4)-adenosyl-N(4)-methyl-2,4-diaminobutanoic acid

Base Information

• Chemical Name: N(4)-adenosyl-N(4)-methyl-2,4-diaminobutanoic acid
• CAS No.: 111770-79-7
• Molecular Formula: C₁₅H₂₃N₇O₅
• Molecular Weight: 381.392
• Mol file: 111770-79-7.mol

Synonyms:Adenosine,5'-[(3-amino-3-carboxypropyl)methylamino]-5'-deoxy-, (S)-

Chemical Property of N(4)-adenosyl-N(4)-methyl-2,4-diaminobutanoic acid

Chemical Property:

• Vapor Pressure: 2.98E-23mmHg at 25°C
• Boiling Point: 744.1°Cat760mmHg
• Flash Point: 403.8°C
• PSA: 185.87000
• Density: 1.79g/cm³
• LogP: -0.95700

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N(4)-adenosyl-N(4)-methyl-2,4-diaminobutanoic acid

There total 7 articles about N(4)-adenosyl-N(4)-methyl-2,4-diaminobutanoic acid 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: 68.0%

(4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one (176847-64-6) → 5'-[N-[(3S)-3-amino-3-carboxypropyl]-N-methylamino]-5'-deoxyadenosine (111770-79-7)

Guidance literature:

With boron trifluoride diethyl etherate; ethanethiol; In dichloromethane; at 20 ℃; for 23h;

DOI:10.1021/jo9907742

Reference yield:

5'-deoxy-5'-methylamino-2',3'-O,O-(1-methylethylidene)adenosine (34245-49-3) → 5'-[N-[(3S)-3-amino-3-carboxypropyl]-N-methylamino]-5'-deoxyadenosine (111770-79-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / (i-Pr)2NEt / acetonitrile / 48 h / 55 °C

2: BF₃*Et₂O, EtSH / CH₂Cl₂ / 24 h / Ambient temperature

With boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; ethanethiol; In dichloromethane; acetonitrile;

DOI:10.1039/cc9960000791

Reference yield:

methyl N4-(2',3'-O-isopropylidene-5'-adenosyl)-N4-methyl-2(R,S)-(trifluoroacetamido)-4-aminobutyrate (116701-00-9,116701-01-0) → N4-(5'-adenosyl)-N4-methyl-2-(R,S),4-diaminobutanoic acid (129828-73-5,111770-79-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Na₂CO₃ / methanol; H₂O / 6 h / 60 °C

2: 0.1 M aq. H₂SO₄ / 264 h / Ambient temperature

With sulfuric acid; sodium carbonate; In methanol; water;

DOI:10.1021/jo00256a010

upstream raw materials:

2-Amino-4-{[(3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-methyl-amino}-butyric acid

methyl N⁴-(2',3'-O-isopropylidene-5'-adenosyl)-N⁴-methyl-2(R,S)-(trifluoroacetamido)-4-aminobutyrate

5'-deoxy-5'-methylamino-2',3'-O,O-(1-methylethylidene)adenosine

((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate

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