(+)-Aerothionin

Base Information

• Chemical Name: (+)-Aerothionin
• CAS No.: 28714-26-3
• Molecular Formula: C₂₄H₂₆Br₄N₄O₈
• Molecular Weight: 818.108
• NSC Number: 177380
• DSSTox Substance ID: DTXSID80951364
• Wikidata: Q82929650
• ChEMBL ID: CHEMBL1999742
• Mol file: 28714-26-3.mol

Synonyms:aerothionin

Chemical Property of (+)-Aerothionin

Chemical Property:

• PKA: 11.14±0.70(Predicted)
• PSA: 160.30000
• Density: 2.05±0.1 g/cm3(Predicted)
• LogP: 2.49460
• Solubility.: Soluble in ethanol;Soluble in DMSO
• XLogP3: 1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 817.84432
• Heavy Atom Count: 40
• Complexity: 1180

Purity/Quality:

95% ^*data from raw suppliers

Aerothionin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(C2(CC(=NO2)C(=O)NCCCCNC(=O)C3=NOC4(C3)C=C(C(=C(C4O)Br)OC)Br)C=C1Br)O)Br
• Uses: Aerothionin is a bromotyrosine derivative with antimycobacterial activity.

Technology Process of (+)-Aerothionin

There total 20 articles about (+)-Aerothionin 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: 40.0%

(5S*,6R*)-methyl 7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro<4.5>deca-2,7,9-triene-3-carboxylate (87580-09-4,87580-10-7) + 1,4-diaminobutane (110-60-1) → aerothionin (28714-26-3,66428-67-9,66428-69-1,87638-40-2)

Guidance literature:

In dichloromethane;

DOI:10.1016/j.tetlet.2004.12.084 DOI:10.1246/bcsj.79.134

Reference yield: 28.0%

1,4-diaminobutane (110-60-1) + (5S,10R)-methyl 7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate (179798-47-1) → Aerothionin (28714-26-3)

Guidance literature:

DOI:10.1016/j.tetlet.2005.11.097

Reference yield: 25.0%

1,4-bis-(7,9-dibromo-8-methoxy-10-oxo-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carbonylamino)-butane (66333-92-4) → aerothionin (28714-26-3,66428-67-9,66428-69-1,87638-40-2)

Guidance literature:

With sodium cyanoborohydride; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1021/jo980860m

upstream raw materials:

1,4-bis-(7,9-dibromo-8-methoxy-10-oxo-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carbonylamino)-butane

N,N'-bis<3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropionyl>-1,4-butanediamine

(5S*,6R*)-methyl 7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro<4.5>deca-2,7,9-triene-3-carboxylate

1,4-diaminobutane

Refernces

• 1、 Ogamino, Takahisa,Obata, Rika,Tomoda, Hiroshi,Nishiyama, Shigeru. "Total synthesis, structural revision, and biological evaluation of calafianin, a marine spiroisoxazoline from the sponge, Aplysina gerardogreeni". . p. 134 - 139. Retrieved 2007/10/03.
• 2、 Wasserman, Harry H.,Wang, Jianji. "Syntheses of the marine metabolites verongamine, hemibastadin-2, and aerothionin using the cyano ylide coupling methodology". . p. 5581 - 5586. Retrieved 2007/10/03.