N6-Benzoyl-2',3'-isopropylideneadenosine

Base Information

• Chemical Name: N6-Benzoyl-2',3'-isopropylideneadenosine
• CAS No.: 39947-04-1
• Molecular Formula: C20H21N5O5
• Molecular Weight: 411.417
• Mol file: 39947-04-1.mol

Synonyms:N6-benzoyl-2',3'-isopropylidene adenosine;2',3'-O,O-isopropylidene-6-N-benzoyladenosine;N-[9-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-benzamide;N6-benzoyl-2′,3′-O-isopropylideneadenosine;N6-benzoyl-2',3'-O-isopropylideneadenosine;N6-monobenzyl 2',3'-O-isopropylidene adenosine;N6-benzoyl-2',3'-isopropylideneadenosine;

Chemical Property of N6-Benzoyl-2',3'-isopropylideneadenosine

Chemical Property:

• Melting Point: 144-146 °C
• PKA: 14.14±0.10(Predicted)
• PSA: 120.62000
• Density: 1.58±0.1 g/cm3(Predicted)
• LogP: 1.56140

Purity/Quality:

97% ^*data from raw suppliers

N6-Benzoyl-2',3'-isopropylideneadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N6-Benzoyl-2',3'-isopropylideneadenosine

There total 16 articles about N6-Benzoyl-2',3'-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: 92.0%

2',3'-isopropylidene adenosine (362-75-4) + benzoyl chloride (98-88-4) → N-6-benzoyl-2',3'-O-isopropylideneadenosine (39947-04-1)

Guidance literature:

2',3'-isopropylidene adenosine; With pyridine; chloro-trimethyl-silane; at 20 ℃; for 0.5h;

benzoyl chloride; at 20 ℃; for 3h; Further stages.;

DOI:10.1021/jo702023s

Reference yield: 89.0%

N-benzoyladenosine (4546-55-8) + 2,2-dimethoxy-propane (77-76-9) → N-6-benzoyl-2',3'-O-isopropylideneadenosine (39947-04-1)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 24h; Reflux; Inert atmosphere;

DOI:10.1080/15257770.2016.1250906

Reference yield: 72.0%

N-benzoyladenosine (4546-55-8) + acetone (67-64-1) → N-6-benzoyl-2',3'-O-isopropylideneadenosine (39947-04-1)

Guidance literature:

With toluene-4-sulfonic acid; at 25 ℃; for 16h;

upstream raw materials:

2',3'-isopropylidene adenosine

benzoyl chloride

2',3'-O-isopropylidene-N⁶,N⁶,5'-O-tribenzoyladenosine

N⁶-benzoyl-7,8-dihydro-2',3'-O-isopropylideneadenosine

Downstream raw materials:

N⁶,N⁶-dibenzoyl-9-(5-deoxy-2,3-O-isopropylidene-β-D-erythropent-4-enofuranosyl)adenine

N⁶,N⁶-dibenzoyl-5'-deoxy-5'-iodo-2',3'-O-isopropylideneadenosine

N-(9-((3aR,4R,6aS)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)benzamide

5'-azido-5'-deoxy-4'-fluoro-2',3'-O-isopropylideneadenosine

Refernces

• 1、 -. "COMPOSITIONS AND METHODS OF MODULATING THE IMMUNE RESPONSE BY ACTIVATING ALPHA PROTEIN KINASE 1". Paragraph 361; 362. . Retrieved 2019/05/15.
• 2、 -. "SUBSTITUTED NUCLEOSIDE ANALOGUES FOR USE AS PRMT5 INHIBITORS". Page/Page column 94. . Retrieved 2017/09/27.