15-acetoxyverrucarol

Base Information

• Chemical Name: 15-acetoxyverrucarol
• CAS No.: 123301-13-3
• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.375
• Mol file: 123301-13-3.mol

Synonyms:

Chemical Property of 15-acetoxyverrucarol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 15-acetoxyverrucarol

There total 1 articles about 15-acetoxyverrucarol 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: 37.0%

acetic anhydride (108-24-7) + verrucarol (2198-92-7,80514-49-4,123301-12-2) → 15-acetoxyverrucarol (2533-38-2,123301-13-3) + 4β,15-diacetoxyverrucarol (2198-94-9,123301-16-6)

Guidance literature:

With pyridine; for 2h; Ambient temperature;

DOI:10.1021/jm00347a018

Reference yield:

15-acetylverrucarol (2533-38-2,123301-13-3) → C57H86O9Si3 (82521-42-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH, HMPA / 1.) THF, 2.) -10 deg C

2: LiOH, H₂O / 1,2-dimethoxy-ethane

3: 1.) NaH, n-Bu₄NI / 1.) THF, 2.) room temp.

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; In 1,2-dimethoxyethane;

DOI:10.1021/jo00138a041

Reference yield:

C17H24O5 (2533-38-2,123301-13-3) → trichodermol (2198-93-8,38757-97-0,74501-22-7)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethylformamide

3: methanesulfonyl chloride / dimethylformamide / 70 °C

4: tri-n-butyltin hydride, benzoyl peroxide

With Perbenzoic acid; tri-n-butyl-tin hydride; methanesulfonyl chloride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)74548-5

upstream raw materials:

acetic anhydride

verrucarol

Downstream raw materials:

C₅₇H₈₆O₉Si₃

trichoverrin B

trichodermol

Refernces