9-(2,3-Bis(hydroxymethyl)-1-cyclobutyl)adenine

Base Information

• Chemical Name: 9-(2,3-Bis(hydroxymethyl)-1-cyclobutyl)adenine
• CAS No.: 124770-85-0
• Molecular Formula: C₁₁H₁₅N₅O₂
• Molecular Weight: 249.272
• ChEMBL ID: CHEMBL30657
• Mol file: 124770-85-0.mol

Synonyms:9-(2,3-bis(hydroxymethyl)-1-cyclobutyl)adenine;C-OXT-A;carbocyclic oxetanocin A;carboxetanocin A;cyclobut A;cyclobut-A

Chemical Property of 9-(2,3-Bis(hydroxymethyl)-1-cyclobutyl)adenine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 563.707°C at 760 mmHg
• Flash Point: 294.72°C
• PSA: 110.08000
• Density: 1.775g/cm³
• LogP: 0.15150
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 249.12257474
• Heavy Atom Count: 18
• Complexity: 305

Purity/Quality:

98%Min ^*data from raw suppliers

CYCLOBUT A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C1N2C=NC3=C(N=CN=C32)N)CO)CO

Technology Process of 9-(2,3-Bis(hydroxymethyl)-1-cyclobutyl)adenine

There total 28 articles about 9-(2,3-Bis(hydroxymethyl)-1-cyclobutyl)adenine 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: 100.0%

9-[(1R,2R,3S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-cyclobutyl]-9H-purin-6-ylamine → (+/-)-9-<(1β,2α,3β)-2,3-bis(hydroxymethyl)-1-cyclobutyl>adenine (124770-85-0,124819-87-0,126187-01-7,129261-92-3,130464-64-1,132294-13-4,132436-35-2,132436-36-3)

Guidance literature:

With acetic acid; at 90 ℃; for 1.5h;

DOI:10.1039/c39930000589

Reference yield: 77.0%

9-[t-2',c-3'-bis(methoxycarbonyl)cyclobut-1'-yl]adenine → (+/-)-9-<(1β,2α,3β)-2,3-bis(hydroxymethyl)-1-cyclobutyl>adenine (124770-85-0,124819-87-0,126187-01-7,129261-92-3,130464-64-1,132294-13-4,132436-35-2,132436-36-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 5h; Heating;

DOI:10.1246/cl.1995.407

Reference yield:

(trans)-3,3-diethoxy-1,2-cyclobutanedicarboxylic acid,diethyl ester (15210-38-5) → (+/-)-9-<(1β,2α,3β)-2,3-bis(hydroxymethyl)-1-cyclobutyl>adenine (124770-85-0,124819-87-0,126187-01-7,129261-92-3,130464-64-1,132294-13-4,132436-35-2,132436-36-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) lithium aluminum hydride / 1.) THF, ether 2.) pyridine

2: p-toluenesulfonic acid / acetone

3: 93 percent / hydroxylamine

4: 20 percent / H₂ / platinum oxide

6: liquid ammonia / 40 °C

7: aq. sodium hydroxide

With sodium hydroxide; lithium aluminium tetrahydride; ammonia; hydrogen; hydroxylamine; toluene-4-sulfonic acid; platinum(IV) oxide; In acetone;

DOI:10.1248/cpb.37.1413

upstream raw materials:

diethoxymethyl acetate

5-amino-4,6-dichloropyridimine

(1β,2α,3β)-2,3-bis(tert-butyldimethylsiloxymethyl)cyclobutylamine

[(1S,2S,4R)-2-Amino-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclobutyl]-methanol

Refernces

• 1、 Jung,Sledeski. "Efficient total synthesis of racemic and optically active cyclobut-A and simple analogues". . p. 589 - 591. Retrieved 2007/10/02.
• 2、 Norbeck, Daniel W.,Kern, Earl,Hayashi, Seiji,Rosenbrook, William,Sham, Hing,et al.. "Cyclobut-A and Cyclobut-G: Broad-Spectrum Antivirial Agents with Potential Utility for the Therapy of AIDS". . p. 1281 - 1285. Retrieved 2007/10/02.