7-Bromo-8-ethyl-3,6,7,8-tetrahydro-alpha-2-penten-4-ynyl-2H-oxocin-2-methanol acetate

Base Information

• Chemical Name: 7-Bromo-8-ethyl-3,6,7,8-tetrahydro-alpha-2-penten-4-ynyl-2H-oxocin-2-methanol acetate
• CAS No.: 3442-58-8
• Molecular Formula: C₁₇H₂₃BrO₃
• Molecular Weight: 355.272
• Nikkaji Number: J15.088F
• Wikidata: Q105374933
• Metabolomics Workbench ID: 166825
• Mol file: 3442-58-8.mol

Synonyms:7-bromo-8-ethyl-3,6,7,8-tetrahydro alpha-2-penten-4-ynyl-2H-oxocin-2-methanol acetate;laurencin

Chemical Property of 7-Bromo-8-ethyl-3,6,7,8-tetrahydro-alpha-2-penten-4-ynyl-2H-oxocin-2-methanol acetate

Chemical Property:

• Vapor Pressure: 2.61E-07mmHg at 25°C
• Boiling Point: 421.4°Cat760mmHg
• Flash Point: 208.7°C
• PSA: 35.53000
• Density: 1.209g/cm³
• LogP: 3.77490
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 354.08306
• Heavy Atom Count: 21
• Complexity: 433

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(CC=CCC(O1)C(CC=CC#C)OC(=O)C)Br
• Isomeric SMILES: CC[C@@H]1[C@H](C/C=C\C[C@@H](O1)[C@@H](C/C=C/C#C)OC(=O)C)Br
• General Description: Laurencin is a brominated natural product characterized by a complex oxocene structure with multiple stereocenters, synthesized through a highly stereoselective and efficient 15-step process involving key transformations such as internal alkylation and the novel use of acetonitrile anion as a synthetic equivalent. The final product, (+)-laurencin, exhibits spectral and optical properties identical to those of the naturally occurring compound.

Technology Process of 7-Bromo-8-ethyl-3,6,7,8-tetrahydro-alpha-2-penten-4-ynyl-2H-oxocin-2-methanol acetate

There total 99 articles about 7-Bromo-8-ethyl-3,6,7,8-tetrahydro-alpha-2-penten-4-ynyl-2H-oxocin-2-methanol acetate 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: 98.0%

2(R),3(S),8(R)-8-[(E),(R)-1-acetoxy-6-(trimethylsilyl)-3-hexen-5-ynyl]-3-bromo-2-ethyl-3,4,7,8-tetrahydro-(2H)-oxocin → (+)-laurencin (3442-58-8,65309-89-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -13 ℃; for 0.0416667h;

DOI:10.1021/ja9709132

Reference yield: 87.0%

Deacetyllaurencin (3352-02-1) + acetyl chloride (75-36-5) → (+)-laurencin (3442-58-8,65309-89-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.tetlet.2005.08.024

Reference yield: 63.0%

Acetic acid (E)-(R)-1-((Z)-(2R,7S,8R)-7-bromo-8-ethyl-3,6,7,8-tetrahydro-2H-oxocin-2-yl)-6-triisopropylsilanyl-hex-3-en-5-ynyl ester → (+)-laurencin (3442-58-8,65309-89-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -10 ℃; for 0.5h;

upstream raw materials:

(E),(1R)-acetic acid 1-[(2R,7R,8R)-8-ethyl-7-hydroxy-3,6,7,8-tetrahydro-2H-oxocin-2-yl]-6-hex-3-en-5-ynyl ester

Deacetyllaurencin

acetyl chloride

(3R,4R)-4-benzyloxy-hept-6-en-3-ol

Refernces

Highly stereoselective and efficient total synthesis of (+)-laurencin

10.1021/ol047877d

The article details the development of a highly stereoselective and efficient total synthesis of the natural product (+)-laurencin from the known oxazolidinone 5 in 15 steps. Key steps in the synthesis include an efficient internal alkylation to form oxocene 3 from 4 and a novel use of acetonitrile anion as a two-carbon acetaldehyde equivalent for direct synthesis of ketone 2 from r-alkoxy amide 3. The synthesis also involves the use of various chemicals such as allylic iodide A, methanol, DMAP, Dibal-H, N,N-dimethyl bromoacetamide, Hooz protocol reagents, KHMDS, lithium anion of acetonitrile, L-Selectride, Wittig reagent phosphorane B, acetic anhydride, DDQ, TBAF, and bromination reagents. These chemicals play crucial roles in the alkylation, reduction, nucleophilic addition, and other transformations necessary to achieve the final product (+)-laurencin, whose spectral characteristics and optical rotation match those of the natural product.