5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide

Base Information

• Chemical Name: 5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide
• CAS No.: 3676-69-5
• Molecular Formula: C12H18N4O5
• Molecular Weight: 298.299
• European Community (EC) Number: 860-143-7
• Nikkaji Number: J1.217.152H
• Mol file: 3676-69-5.mol

Synonyms:5-AMino-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)iMidazole-4-carboxaMide;5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide

Chemical Property of 5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide

Chemical Property:

• PSA: 135.84000
• LogP: 0.43940
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 298.12771969
• Heavy Atom Count: 21
• Complexity: 434

Purity/Quality:

97% ^*data from raw suppliers

5-Amino-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)N3C=NC(=C3N)C(=O)N)CO)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C=NC(=C3N)C(=O)N)CO)C
• Uses: Protected 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranoside (A611700), a nucleoside analogue that is able to enter nucleoside pools and is able to significantly increase levels of adenosine during periods of ATP breakdown. Adenosine-regulating agents (ARAs) have been recognized for therapeutic potential in myocardial ischemia. Cardioprotective.

Technology Process of 5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide

There total 7 articles about 5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide 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: 78.0%

AICA riboside (2627-69-2) + acetone (67-64-1) → 5-Amino-1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-imidazole-4-carboxylic acid amide (3676-69-5)

Guidance literature:

With toluene-4-sulfonic acid; orthoformic acid triethyl ester; for 2h; Ambient temperature;

Reference yield:

1-(2,4-dinitrophenyl)-2',3'-O-isopropylideneinosine (924887-44-5) → 5-Amino-1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-imidazole-4-carboxylic acid amide (3676-69-5)

Guidance literature:

1-(2,4-dinitrophenyl)-2',3'-O-isopropylideneinosine; With dmap; In pyridine; at 20 ℃; for 24h;

With ethylenediamine; In N,N-dimethyl-formamide; at 50 ℃; for 8h;

With trifluoroacetic acid; In dichloromethane; Further stages.;

DOI:10.1016/j.tetlet.2006.11.085

Reference yield:

2',3',5'-tri-O-acetylinosine (3181-38-2) → 5-Amino-1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-imidazole-4-carboxylic acid amide (3676-69-5)

Guidance literature:

Multi-step reaction with 4 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C

2: ammonia / water; methanol / 1 h / 20 °C

3: sodium hydroxide / 1 h / Reflux

4: perchloric acid / 4 h / 25 °C

With perchloric acid; ammonia; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In methanol; dichloromethane; water;

upstream raw materials:

AICA riboside

acetone

1-(2,4-dinitrophenyl)-2',3'-O-isopropylideneinosine

2',3',5'-tri-O-acetylinosine

Downstream raw materials:

(5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carbonyl)-L-aspartic acid

[Carbamoyl-((3aR,4R,6R,6aR)-6-{(4-chloro-phenoxy)-[((Z)-octadec-9-enyl)oxy]-phosphoryloxymethyl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylcarbamoyl)-methyl]-carbamic acid tert-butyl ester

(Carbamoyl-{(3aR,4R,6R,6aR)-6-[(4-chloro-phenoxy)-hexadecyloxy-phosphoryloxymethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylcarbamoyl}-methyl)-carbamic acid tert-butyl ester

Phosphoric acid (2R,3S,4R,5R)-5-(4-carbamoyl-5-hydroxy-imidazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 4-chloro-phenyl ester (Z)-octadec-9-enyl ester

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 3676-69-5 5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide

Send

Send

Metric Ton KG G Pound L ML

Send

Send