20-Deoxyingenol 3-angelate

Base Information

• Chemical Name: 20-Deoxyingenol 3-angelate
• CAS No.: 75567-38-3
• Molecular Formula: C₂₅H₃₄O₅
• Molecular Weight: 414.542
• Mol file: 75567-38-3.mol

Synonyms:2-Butenoicacid, 2-methyl-,1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-1,1,4,7,9-pentamethyl-11-oxo-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-6-ylester, [1aR-[1aa,2b,5b,5ab,6b(Z),8aa,9a,10aa]]-; 1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecene,2-butenoic acid deriv.; 20-Deoxyingenol 3-angelate; 3-Angelyl-20-deoxyingenol;Euphorbia factor H8; PEP 006

Chemical Property of 20-Deoxyingenol 3-angelate

Chemical Property:

• PSA: 83.83000
• LogP: 3.35990

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

20-Deoxyingenol3-angelate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 20-Deoxyingenol 3-angelate

There total 4 articles about 20-Deoxyingenol 3-angelate 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: 33.8%

(Z)-2-methyl-2-butenoic anhydride (94487-74-8) + (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one (54706-99-9) → 3-tigloyl-20-deoxyingenol (75567-38-3) + 3-O-angeloyl-20-deoxyingenol (75567-38-3)

Guidance literature:

With pyridine; dmap; at 40 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.ejmech.2018.07.020

Reference yield: 33.8%

(Z)-2-methyl-2-butenoic anhydride (94487-74-8) + (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one (54706-99-9) → 3-tigloyl-20-deoxyingenol (75567-38-3) + 3-O-angeloyl-20-deoxyingenol (75567-38-3)

Guidance literature:

With pyridine; dmap; at 40 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.ejmech.2018.07.020

Reference yield:

5-O-benzoyl-20-deoxyingenol → 3-tigloyl-20-deoxyingenol (75567-38-3) + 3-O-angeloyl-20-deoxyingenol (75567-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / methanol / 3 h / 20 °C

2: dmap; pyridine / 24 h / 40 °C / Inert atmosphere

With pyridine; dmap; potassium carbonate; In methanol;

DOI:10.1016/j.ejmech.2018.07.020

upstream raw materials:

(Z)-2-methyl-2-butenoic anhydride

(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

Downstream raw materials:

ingenol mebutate

Refernces