Ingenol-5,20-acetonide-3-O-angelate

Base Information

• Chemical Name: Ingenol-5,20-acetonide-3-O-angelate
• CAS No.: 87980-68-5
• Molecular Formula: C₂₈H₃₈O₆
• Molecular Weight: 470.606
• Mol file: 87980-68-5.mol

Synonyms:Ingenol-5,20-acetonide-3-O-angelate;Ingenol 5,20-acetonide 3-angelate

Chemical Property of Ingenol-5,20-acetonide-3-O-angelate

Chemical Property:

• Boiling Point: 582.2±50.0 °C(Predicted)
• PKA: 11.38±0.70(Predicted)
• PSA: 82.06000
• Density: 1.21±0.1 g/cm3(Predicted)
• LogP: 4.13060

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ingenol5,20-Acetonide-3-O-angelate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ingenol 5,20-Acetonide-3-O-angelate is a derivative of Ingenol (I655795), the analogue of Ingenol 3-Angelate (I655800), which has anti-tumor activity when used topically for the treatment of actinic keratosis.

Technology Process of Ingenol-5,20-acetonide-3-O-angelate

There total 21 articles about Ingenol-5,20-acetonide-3-O-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: 95.7%

(Z)-2-methyl-2-butenoic anhydride (94487-74-8) + (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) → 3-O-angeloyl-5,20-O-isopropylideneingenol (87980-68-5)

Guidance literature:

With caesium carbonate; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1016/j.ejmech.2018.07.020

Reference yield: 84.0%

Tiglic acid (80-59-1) + (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-5,20-acetonide-3-tiglate (1356490-35-1,87980-68-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In chloroform-d1; dichloromethane; at 20 ℃; for 24h;

DOI:10.1055/s-0032-1317415

Reference yield: 76.0%

(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride (137601-32-2) + (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) → 3-O-angeloyl-5,20-O-isopropylideneingenol (87980-68-5)

Guidance literature:

With sodium hydrogencarbonate; In toluene; at 100 ℃; for 22h;

upstream raw materials:

acetone

ingenol mebutate

Angelic acid

(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

Downstream raw materials:

ingenol mebutate

ingenol-3-tigliate

ingenol 20-acetate-3-angelate

Refernces

• 1、 Ohyoshi, Takayuki,Tamura, Yuki,Hayakawa, Ichiro,Hirai, Go,Miyazawa, Yamato,Funakubo, Shota,Sodeoka, Mikiko,Kigoshi, Hideo. "Total synthesis of natural derivatives and artificial analogs of 13-oxyingenol and their biological evaluation". . p. 11426 - 11437. Retrieved 2016/12/18.
• 2、 Liang, Xifu,Grue-Sorensen, Gunnar,Petersen, Anders Klarskov,H?gberg, Thomas. "Semisynthesis of ingenol 3-angelate (PEP005): Efficient stereoconservative angeloylation of alcohols". . p. 2647 - 2652. Retrieved 2013/01/15.