Destruxin E

Base Information

• Chemical Name: Destruxin E
• CAS No.: 76689-14-0
• Molecular Formula: C29H47N5O8
• Molecular Weight: 593.71
• NSC Number: 361127
• DSSTox Substance ID: DTXSID70997998
• Wikidata: Q105179719
• ChEMBL ID: CHEMBL2005348
• Mol file: 76689-14-0.mol

Synonyms:cyclo(N-methyl-L-alanyl-beta-alanyl-4,5-anhydro-3-deoxy-D-erythro-pentonoyl-L-prolyl-L-isoleucyl-N-methyl-L-valyl);destruxin DE;destruxin E;E-destruxin

Chemical Property of Destruxin E

Chemical Property:

• Vapor Pressure: 6.03E-34mmHg at 25°C
• Boiling Point: 909.6°C at 760 mmHg
• Flash Point: 503.9°C
• PSA: 157.96000
• Density: 1.24g/cm³
• LogP: 0.53010
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 593.34246347
• Heavy Atom Count: 42
• Complexity: 1050

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C1C(=O)N(C(C(=O)N(C(C(=O)NCCC(=O)OC(C(=O)N2CCCC2C(=O)N1)CC3CO3)C)C)C(C)C)C

Technology Process of Destruxin E

There total 18 articles about Destruxin E 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: 64.0%

C36H55N5O11S (1240507-88-3) → destruxin E (76689-14-0)

Guidance literature:

With potassium carbonate; In isopropyl alcohol; at 0 - 50 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jo402437z

Reference yield:

C32H55N5O10 (1240507-78-1) → destruxin E (76689-14-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 4-(dimethylamino)pyridine N-oxide; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 48 h / 20 - 30 °C / Inert atmosphere

2: hydrogenchloride / water; 1,4-dioxane / 2 h / 0 °C

3: dmap; triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

4: potassium carbonate / isopropyl alcohol / 4 h / 0 - 50 °C / Inert atmosphere

With hydrogenchloride; dmap; 2-methyl-6-nitrobenzoic anhydride; 4-(dimethylamino)pyridine N-oxide; potassium carbonate; triethylamine; In 1,4-dioxane; dichloromethane; water; isopropyl alcohol;

DOI:10.1021/jo402437z

Reference yield:

C32H53N5O9 (1240507-87-2) → destruxin E (76689-14-0)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / water; 1,4-dioxane / 2 h / 0 °C

2: dmap; triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

3: potassium carbonate / isopropyl alcohol / 4 h / 0 - 50 °C / Inert atmosphere

With hydrogenchloride; dmap; potassium carbonate; triethylamine; In 1,4-dioxane; dichloromethane; water; isopropyl alcohol;

DOI:10.1021/jo402437z

upstream raw materials:

C₃₆H₅₅N₅O₁₁S

C₄₃H₈₁N₅O₁₀Si₂

C₃₂H₅₅N₅O₁₀

C₃₂H₅₃N₅O₉

Refernces

• 1、 Yoshida, Masahito,Sato, Hiroshi,Ishida, Yoshitaka,Nakagawa, Hiroshi,Doi, Takayuki. "Scalable solution-phase synthesis of the biologically active cyclodepsipeptide destruxin E, a potent negative regulator of osteoclast morphology". . p. 296 - 306. Retrieved 2014/01/17.