aerothionin

Base Information

• Chemical Name: aerothionin
• CAS No.: 66428-69-1
• Molecular Formula: C₂₄H₂₆Br₄N₄O₈
• Molecular Weight: 818.108
• Mol file: 66428-69-1.mol

Synonyms:

Chemical Property of aerothionin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of aerothionin

There total 16 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: 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

Reference yield:

methyl (2-benzyloxy-4-methoxyphenyl)acetate (209404-16-0) → aerothionin (28714-26-3,66428-67-9,66428-69-1,87638-40-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / H₂ / Pd/C / methanol / 7 h / 760 Torr / Ambient temperature

2: 90 percent / pyridinium hydrobromide perbromide / CH₂Cl₂; pyridine / 1 h / Ambient temperature

3: 93 percent / (n-Bu)4NI, 18-crown-6 / acetone / 3 h / Heating

4: 94 percent / aq. NaOH / methanol / 1.5 h / Ambient temperature

5: 88 percent / EDCI / CH₂Cl₂ / 4 h / Ambient temperature

6: 1.) O₃ / 1.) CH₂Cl_2. -78 deg C, 5 min, 2.) CH₂Cl₂, room temperature, 1 h

7: 95 percent / NH₂OH*HCl, NaOAc / ethanol; tetrahydrofuran / 4 h / 50 - 60 °C

8: 92 percent / TFA / CH₂Cl₂ / 0.33 h / Ambient temperature

9: 70 percent / 2,4,4,6-tetrabromo-2,5-cyclohexadienone / acetonitrile / 24 h / Ambient temperature

10: 25 percent / NaCNBH₃, TFA / CH₂Cl₂ / 0.33 h / 0 °C

With sodium hydroxide; 18-crown-6 ether; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; hydroxylamine hydrochloride; hydrogen; sodium acetate; pyridinium hydrobromide perbromide; tetra-(n-butyl)ammonium iodide; sodium cyanoborohydride; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; acetone; acetonitrile;

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、 Nishiyama,Yamamura. "Total syntheses of (±)-aerothionin, (±)-homoaerothionin, and (±)-aerophobin-1". . p. 3453 - 3456. Retrieved 2007/10/02.