ingenol-3-tigliate

Base Information

• Chemical Name: ingenol-3-tigliate
• CAS No.: 1356187-27-3
• Molecular Formula: C₂₅H₃₄O₆
• Molecular Weight: 430.541
• Mol file: 1356187-27-3.mol

Synonyms:

Chemical Property of ingenol-3-tigliate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ingenol-3-tigliate

There total 11 articles about ingenol-3-tigliate 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: 99.0%

Angelic acid (565-63-9) + (6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one (77573-43-4) → ingenol-3-tigliate (1356187-27-3,849146-39-0) + ingenol mebutate (75567-37-2,849146-39-0)

Guidance literature:

With hydrogenchloride; water; In methanol; at 20 ℃; for 1h;

DOI:10.1055/s-0032-1317415

Reference yield:

3-O-angeloyl-5,20-O-isopropylideneingenol (87980-68-5) → ingenol-3-tigliate (1356187-27-3,849146-39-0) + ingenol mebutate (75567-37-2,849146-39-0)

Guidance literature:

With methanesulfonic acid; water; In tetrahydrofuran; at 20 ℃; for 72h; Product distribution / selectivity;

Reference yield:

ingenol (30220-46-3) → ingenol-3-tigliate (1356187-27-3,849146-39-0) + ingenol mebutate (75567-37-2,849146-39-0)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / 1.5 h / 20 °C

2: sodium hydrogencarbonate / toluene / 22 h / 100 °C

3: water; methanesulfonic acid / tetrahydrofuran / 72 h / 20 °C

With methanesulfonic acid; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; toluene;

upstream raw materials:

Angelic acid

ingenol

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

3-O-angeloyl-5,20-O-isopropylideneingenol