Clonostachydiol

Base Information

• Chemical Name: Clonostachydiol
• CAS No.: 147317-35-9
• Molecular Formula: C₁₄H₂₀O₆
• Molecular Weight: 284.309
• Hs Code.: 29419000
• DSSTox Substance ID: DTXSID001017523
• Wikidata: Q27138388
• Mol file: 147317-35-9.mol

Synonyms:clonostachydiol

Chemical Property of Clonostachydiol

Chemical Property:

• Vapor Pressure: 1.67E-15mmHg at 25°C
• Boiling Point: 572.7 °C at 760 mmHg
• Flash Point: 216 °C
• PSA: 93.06000
• Density: 1.165 g/cm³
• LogP: 0.47780
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 284.12598835
• Heavy Atom Count: 20
• Complexity: 401

Purity/Quality:

98% ^*data from raw suppliers

Clonostachydiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C=CC(=O)OC(C(C=CC(=O)O1)O)C)O
• Isomeric SMILES: C[C@@H]1CC[C@@H](/C=C/C(=O)O[C@@H]([C@H](/C=C/C(=O)O1)O)C)O
• Uses: Clonostachydiol is an anthelmintic macrodiolide from Clonostachys cylindrospora. Clonostachydiol is a potential lead compound for developing formulations against the intestinal nematodes of ruminants.

Technology Process of Clonostachydiol

There total 26 articles about Clonostachydiol 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%

C22H38O7Si (1105507-64-9) → (3E,9E)-(5S,6R,11R,14R)-5,11-Dihydroxy-6,14-dimethyl-1,7-dioxa-cyclotetradeca-3,9-diene-2,8-dione (147317-35-9)

Guidance literature:

With hydrogenchloride; water; In methanol; at 20 ℃;

DOI:10.1055/s-0028-1087296

Reference yield: 80.0%

(4R,7R,E)-((2R,3S)-3-hydroxypent-4-en-2-yl) 7-(acryloyloxy)-4-hydroxyoct-2-enoate (1369492-93-2) → (3E,9E)-(5S,6R,11R,14R)-5,11-Dihydroxy-6,14-dimethyl-1,7-dioxa-cyclotetradeca-3,9-diene-2,8-dione (147317-35-9)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In toluene; at 80 ℃; for 0.5h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.01.014

Reference yield: 70.0%

(3E,9E)-(5S,6R,11R,14R)-5-Allyloxy-11-hydroxy-6,14-dimethyl-1,7-dioxa-cyclotetradeca-3,9-diene-2,8-dione (161277-65-2) → (3E,9E)-(5S,6R,11R,14R)-5,11-Dihydroxy-6,14-dimethyl-1,7-dioxa-cyclotetradeca-3,9-diene-2,8-dione (147317-35-9)

Guidance literature:

With toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; at 60 ℃;

DOI:10.1016/0040-4039(94)02196-I

upstream raw materials:

(3E,9E)-(5S,6R,11R,14R)-5-Allyloxy-11-hydroxy-6,14-dimethyl-1,7-dioxa-cyclotetradeca-3,9-diene-2,8-dione

(E)-(4S,5R)-4-Allyloxy-5-hydroxy-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester

(E)-(4S,5R)-4-Allyloxy-5-formyloxy-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester

Chloro-acetic acid (3E,9E)-(5S,6R,11R,14R)-5-allyloxy-6,14-dimethyl-2,8-dioxo-1,7-dioxa-cyclotetradeca-3,9-dien-11-yl ester

Downstream raw materials:

C₁₄H₁₈O₆

Refernces

• 1、 Yadav,Swamy,Subba Reddy. "A stereoselective approach for the total synthesis of clonostachydiol". scheme or table. p. 2773 - 2776. Retrieved 2009/04/16.
• 2、 Rao, A. V. Rama,Murthy, V. S.,Sharma, G. V. M.. "The first synthesis and determination of absolute stereochemistry of clonostachydiol - Part II". . p. 143 - 146. Retrieved 2007/10/02.