N2-acetamido-6-benzyloxypurine

Base Information

• Chemical Name: N2-acetamido-6-benzyloxypurine
• CAS No.: 92193-74-3
• Molecular Formula: C14H13N5O2
• Molecular Weight: 283.29
• Hs Code.: 2932999099
• ChEMBL ID: CHEMBL117601
• DSSTox Substance ID: DTXSID30566462
• Nikkaji Number: J578.078K
• Wikidata: Q72497606
• Mol file: 92193-74-3.mol

Synonyms:N2-acetamido-6-benzyloxypurine;92193-74-3;N-(6-phenylmethoxy-7H-purin-2-yl)acetamide;2-ACETYLAMINO-6-BENZYLOXY-9H-PURINE;CHEMBL117601;SCHEMBL3303363;DTXSID30566462;MHBWNOBMRPRKSD-UHFFFAOYSA-N;N-(6-phenylmethoxy-7H-purin-2-yl)ethanamide;N-[6-(phenylmethoxy)-1H-purin-2-yl]-acetamide;A844168;N-[6-(BENZYLOXY)-7H-PURIN-2-YL]ACETAMIDE

Chemical Property of N2-acetamido-6-benzyloxypurine

Chemical Property:

• PSA: 92.79000
• Density: 1.382 g/cm³
• LogP: 1.96330
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 283.10692467
• Heavy Atom Count: 21
• Complexity: 361

Purity/Quality:

99% ^*data from raw suppliers

2-ACETYLAMINO-6-BENZYLOXY-9H-PURINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=NC2=C(C(=N1)OCC3=CC=CC=C3)NC=N2

Technology Process of N2-acetamido-6-benzyloxypurine

There total 6 articles about N2-acetamido-6-benzyloxypurine 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:

C16H15N5O3 → N2-acetyl-O6-benzylguanine (92193-74-3)

Guidance literature:

With water; In ethanol; Reflux;

DOI:10.1021/acs.orglett.9b03707

Reference yield:

C9H9N5O3 → N2-acetyl-O6-benzylguanine (92193-74-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate

2: water / ethanol / Reflux

With di-isopropyl azodicarboxylate; water; triphenylphosphine; In ethanol;

DOI:10.1021/acs.orglett.9b03707

Reference yield:

guanine (133310-37-9) → N2-acetyl-O6-benzylguanine (92193-74-3)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-dimethyl acetamide / 160 °C

2: triphenylphosphine; di-isopropyl azodicarboxylate

3: water / ethanol / Reflux

With di-isopropyl azodicarboxylate; water; triphenylphosphine; In ethanol; N,N-dimethyl acetamide;

DOI:10.1021/acs.orglett.9b03707

upstream raw materials:

acetic anhydride

2-Amino-6-benzyloxypurine

2-Amino-6-chloropurin

benzyl alcohol

Downstream raw materials:

N-[6-Benzyloxy-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-acetamide

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(2-acetylamino-6-benzyloxy-purin-9-yl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester

Refernces

• 1、 Cheung, Adrian Wai-Hing,Sidduri, Achyutharao,Garofalo, Lisa M.,Goodnow Jr., Robert A.. "An unusual solvent effect on the regiochemical outcome (N-9 versus N-7) of guanine glycosylation using Robins' reagent (2-N-acetyl-6-O- diphenylcarbamoylguanine)". . p. 3303 - 3307. Retrieved 2007/10/03.