5'-Carboxy-2',3'-O-isopropylideneadenosine

Base Information

• Chemical Name: 5'-Carboxy-2',3'-O-isopropylideneadenosine
• CAS No.: 811431-33-1
• Molecular Formula: C₁₄H₁₇N₅O₅
• Molecular Weight: 335.319

Synonyms:5'-Carboxy-2',3'-O-isopropylideneadenosine;1-(6-Amino-9H-purin-9-yl)-1,5-dideoxy-2,3-O-(1-methylethylidene)-beta-D-ribo-hexofuranuronic acid

Chemical Property of 5'-Carboxy-2',3'-O-isopropylideneadenosine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 635.537°C at 760 mmHg
• Flash Point: 338.161°C
• PSA: 134.61000
• Density: 1.829g/cm³
• LogP: 0.88190

Purity/Quality:

97% ^*data from raw suppliers

5'-CARBOXY-2',3'-O-ISOPROPYLIDENE-ADENOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5'-Carboxy-2',3'-O-isopropylideneadenosine

There total 5 articles about 5'-Carboxy-2',3'-O-isopropylideneadenosine 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%

[(3aR,4R,6R,6aR)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetic acid (851636-82-3) → [(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetic acid (811431-33-1)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/j.bmcl.2004.09.050

Reference yield:

N6-benzoyl-2',3'-isopropylidene-5'-carboxylic acid-5'-deoxy-adenosine (119750-97-9) → [(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetic acid (811431-33-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / SOCl₂ / CH₂Cl₂

2: 80 percent / CH₂Cl₂

3: 47 percent / H₂O; PhCO₂Ag / dioxane / Heating

4: 96 percent / MeONa / methanol

With thionyl chloride; water; sodium methylate; silver benzoate; In 1,4-dioxane; methanol; dichloromethane; 3: Wolff rearrangement;

DOI:10.1016/j.bmcl.2004.09.050

Reference yield:

N-6-benzoyl-2',3'-O-isopropylideneadenosine (39947-04-1) → [(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetic acid (811431-33-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / TEMPO; bis(acetoxy)iodobenzene / acetonitrile; H₂O

2: 100 percent / SOCl₂ / CH₂Cl₂

3: 80 percent / CH₂Cl₂

4: 47 percent / H₂O; PhCO₂Ag / dioxane / Heating

5: 96 percent / MeONa / methanol

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; thionyl chloride; [bis(acetoxy)iodo]benzene; water; sodium methylate; silver benzoate; In 1,4-dioxane; methanol; dichloromethane; water; acetonitrile; 4: Wolff rearrangement;

DOI:10.1016/j.bmcl.2004.09.050

upstream raw materials:

[(3aR,4R,6R,6aR)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetic acid

N⁶-benzoyl-2',3'-isopropylidene-5'-carboxylic acid-5'-deoxy-adenosine

N-6-benzoyl-2',3'-O-isopropylideneadenosine

(3aS,4S,6R,6aR)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl chloride

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