8-Benzylthio-N-butyl cyclic amp

Base Information

• Chemical Name: 8-Benzylthio-N-butyl cyclic amp
• CAS No.: 56583-64-3
• Molecular Formula: C21H26N5O6PS
• Molecular Weight: 507.5
• ChEMBL ID: CHEMBL3142439
• Nikkaji Number: J395.245B
• Mol file: 56583-64-3.mol

Synonyms:8-benzylthio-N(6)-n-butyladenosine cyclic-3,5'-monophosphate;8-benzylthio-N-butyl cyclic AMP;8-BTBCA;N(6)-n-butyl-8-BTCAMP

Chemical Property of 8-Benzylthio-N-butyl cyclic amp

Chemical Property:

• PSA: 175.96000
• LogP: 3.17770
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 507.13414174
• Heavy Atom Count: 34
• Complexity: 736

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCNC1=C2C(=NC=N1)N(C(=N2)SCC3=CC=CC=C3)C4C(C5C(O4)COP(=O)(O5)O)O
• Isomeric SMILES: CCCCNC1=C2C(=NC=N1)N(C(=N2)SCC3=CC=CC=C3)[C@H]4[C@@H]([C@H]5[C@H](O4)COP(=O)(O5)O)O

Technology Process of 8-Benzylthio-N-butyl cyclic amp

There total 8 articles about 8-Benzylthio-N-butyl cyclic amp 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: 61.0%

2'-O-acetyl-8-(benzylthio)-6-chloro-9-(β-D-ribofuranosyl)purine cyclic 3',5'-phosphate sodium salt (55628-39-2) + N-butylamine (109-73-9,85404-21-3) → 8-(benzylthio)-6-(n-butylamino)-9-(β-D-ribofuranosyl)purine cyclic 3',5'-phosphate (56583-64-3)

Guidance literature:

In water; Ambient temperature;

DOI:10.1021/jm00177a007

Reference yield:

cAMP (60-92-4) → 8-(benzylthio)-6-(n-butylamino)-9-(β-D-ribofuranosyl)purine cyclic 3',5'-phosphate (56583-64-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 146 g / 1,5-diazabicyclo<5.4.0>undec-5-ene, 2,6-lutidine / dimethylformamide / 5 h / 60 °C

2: 1 N aq. NaOH / 2 h / 75 °C

3: H₂ / 5percent Pt/C / acetic acid; H₂O / 5 h / 2068.6 Torr

4: Br₂, NaOAc / acetic acid; H₂O / 72 h / Ambient temperature

5: 30percent aq. NaOH / acetic acid; H₂O / 1 h / 70 °C

With 2,6-dimethylpyridine; sodium hydroxide; hydrogen; bromine; sodium acetate; 1,5-Diazabicyclo[5.4.0]undec-5-ene; platinum on activated charcoal; In water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm00177a007

Reference yield:

(4aR,6R,7R,7aS)-6-{6-[((E)-But-2-enyl)amino]-purin-9-yl}-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol (72549-57-6) → 8-(benzylthio)-6-(n-butylamino)-9-(β-D-ribofuranosyl)purine cyclic 3',5'-phosphate (56583-64-3)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 5percent Pt/C / acetic acid; H₂O / 5 h / 2068.6 Torr

2: Br₂, NaOAc / acetic acid; H₂O / 72 h / Ambient temperature

3: 30percent aq. NaOH / acetic acid; H₂O / 1 h / 70 °C

With sodium hydroxide; hydrogen; bromine; sodium acetate; platinum on activated charcoal; In water; acetic acid;

DOI:10.1021/jm00177a007

upstream raw materials:

2'-O-acetyl-8-(benzylthio)-6-chloro-9-(β-D-ribofuranosyl)purine cyclic 3',5'-phosphate sodium salt

N-butylamine

8-bromo-6-(n-butylamino)-9-(β-D-ribofuranosyl)purine cyclic 3',5'-phosphate

phenylmethanethiol

Refernces

• 1、 Miller, Jon P.,Boswell, Kay H.,Meyer, Rich B.,Christensen, Leon F.,Robins, Roland K.. "Synthesis and Enzymatic and Inotropic Activity of Some New 8-Substituted and 6,8-Disubstituted Derivatives of Adenosine Cyclic 3',5'-Monophosphate". . p. 242 - 251. Retrieved 2007/10/02.