(1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate

Base Information

• Chemical Name: (1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate
• CAS No.: 83036-62-8
• Molecular Formula: C₃₄H₅₄O₆
• Molecular Weight: 558.799
• Mol file: 83036-62-8.mol

Synonyms:(1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-Dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate;

Chemical Property of (1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate

Chemical Property:

• Vapor Pressure: 3.39E-19mmHg at 25°C
• Refractive Index: 1.544
• Boiling Point: 642.1 °C at 760 mmHg
• Flash Point: 192.1 °C
• Density: 1.12 g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate

There total 6 articles about (1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate 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: 82.0%

ingenol-5β,20-O,O-isopropylidene-3β-O-myristinate (83036-74-2) → 3-O-tetradecanoylingenol (83036-62-8)

Guidance literature:

With perchloric acid; In methanol; for 0.75h;

Reference yield: 80.0%

3-O-tetradecanoylingenol-20-aldehyde (143725-46-6) → 3-O-tetradecanoylingenol (83036-62-8)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In ethanol; at 0 ℃; for 0.0833333h;

Reference yield:

(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-tetradecanoylingenol (83036-62-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-(N,N-dimethylamino)pyridine / toluene / 2 h

2: 82 percent / 70 percent HClO₄ / methanol / 0.75 h

With dmap; perchloric acid; In methanol; toluene;

upstream raw materials:

3-O-tetradecanoylingenol-20-aldehyde

ingenol-5β,20-O,O-isopropylidene-3β-O-myristinate

(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

tetradecanoyl chloride

Refernces

• 1、 Roeser, H.,Sorg, B.,Hecker, E.. "On the Chemistry of Ingenol, V. Preparation of Tritium-Labeled 3-O-Tetradecanoylingenol (-3-TI)". . p. 1026 - 1030. Retrieved 2007/10/02.