STACHYBOTRYLACTAM

Base Information

• Chemical Name: STACHYBOTRYLACTAM
• CAS No.: 163391-76-2
• Molecular Formula: C₂₃H₃₁NO₄
• Molecular Weight: 385.503
• Mol file: 163391-76-2.mol

Synonyms:STACHYBOTRYLACTAM;2-deoxy F1839A

Chemical Property of STACHYBOTRYLACTAM

Chemical Property:

• Melting Point: 210℃ (Decomposition) (ethyl acetate )
• Boiling Point: 630.0±55.0 °C(Predicted)
• PKA: 9.39±0.70(Predicted)
• PSA: 82.28000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 3.55300
• Storage Temp.: ?20°C

Purity/Quality:

NLT 98% ^*data from raw suppliers

Stachybotrylactam ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Stachybotrylactam is an unusual, spirodihydrobenzofuranlactam mycotoxin isolated from a Stachybotrys sp., showing immunosuppressant and weak HIV protease activity. Members of this structural class show diverse activity including antiviral, endothelin and pancreatic cholesterase inhibition. Stachybotrylactam is an unusual spirodihydrobenzofuranlactam mycotoxin isolated from a Stachybotrys sp. that has immunosuppressant and weak HIV protease activity. Members of this structural class show diverse activity including antiviral, endothelin and pancreatic cholesterase inhibition.

Technology Process of STACHYBOTRYLACTAM

There total 20 articles about STACHYBOTRYLACTAM 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: 85.0%

[1'(2)R,2'R,4'aS,6'R,8'aS]-6'-hydroxy-7-cyano-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester (541501-18-2) → stachybotrylactam (163391-76-2)

Guidance literature:

[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-6'-hydroxy-7-cyano-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester; With hydrogen; platinum(IV) oxide; In ethanol; chloroform;

With sodium hydroxide; In water;

DOI:10.1021/ol030039j

Reference yield:

chartarolide C → 2-chloro-3,7-dihydroxy-4-(hydroxymethyl)-1,9-dimethyl-8-(3-methylbut-2-enyl)-11H-dibenzo[b,e][1,4]dioxepin-2-one (68455-11-8) + stachybotrylactam (163391-76-2)

Guidance literature:

With sulfuric acid; In methanol; at 90 ℃; for 2h;

DOI:10.1016/j.tetlet.2017.03.079

Reference yield:

(-)-(4aS,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone (155486-89-8) → stachybotrylactam (163391-76-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -20 - 0 °C

1.2: tetrahydrofuran; hexane / 0.5 h / 0 °C

2.1: molecular sieves 4 Angstroem; benzyltrimethylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

2.2: 2.16 g / hydrazine; AcOH / ethanol / Heating

3.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: tetrahydrofuran; hexane / 2 h / -78 - 0 °C

4.1: 1.81 g / NaBH₃CN; ZnI₂ / CH₂Cl₂ / 4 h / 0 °C

5.1: thionyl chloride / 2.5 h / Heating

6.1: 66 mg / Raney Ni; hydrogen / tetrahydrofuran; H₂O / 16 h

7.1: hydrogen / Pd/C / ethanol / 8 h

8.1: 389 mg / Amberlyst 15 / CH₂Cl₂ / 72 h / 0 °C

9.1: 96 percent / imidazole / CH₂Cl₂ / 20 °C

10.1: NBS / CH₂Cl₂ / 10 h / 20 °C

10.2: 45 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

11.1: 95 percent / K₂CO₃; n-Bu₄NI / acetonitrile / 20 °C

12.1: 94 percent / dimethylformamide / 4 h / 100 °C

13.1: hydrogen / PtO₂ / ethanol; CHCl₃

14.1: 50 mg / NaOH / H₂O / 0.17 h / pH 10

With 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; n-butyllithium; thionyl chloride; Amberlyst 15; 4 A molecular sieve; hydrogen; tetra-(n-butyl)ammonium iodide; trimethyl(benzyl)ammonium fluoride; nickel; sodium cyanoborohydride; potassium carbonate; zinc(II) iodide; lithium diisopropyl amide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-6'-hydroxy-7-cyano-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester

(-)-(4aS,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone

[2R,4aS,6R,8aS]-6-benzyloxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde

[1'⁽²⁾R,2'R,4'aS,6'R,8'aS]-4,6'-dihydroxy-3',4',4'a,5',6',7',8',8'a-octahydro-2',5',5',8'a-tetramethylspiro[benzofuran-2(3H),1'(2'H)-naphthalene]-6-carboxylic acid methyl ester

Refernces

• 1、 Kende, Andrew S.,Deng, Wei-Ping,Zhong, Min,Guo, Xiao-Chuan. "Enantioselective total synthesis and structure revision of spirodihydrobenzofuranlactam 1. Total synthesis of stachybotrylactam". . p. 1785 - 1788. Retrieved 2007/10/03.