Ropa

Base Information

• Chemical Name: Ropa
• CAS No.: 57852-42-3
• Molecular Formula: C28H32 O6
• Molecular Weight: 464.558
• European Community (EC) Number: 810-212-2
• DSSTox Substance ID: DTXSID40973441
• Wikidata: Q82957359
• ChEMBL ID: CHEMBL485800
• Mol file: 57852-42-3.mol

Synonyms:ROPA;57852-42-3;ROP;Daphnetoxin, 6,7-deepoxy-6,7-didehydro-5-deoxy-21-dephenyl-21-(phenylmethyl)-;(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-3a,3b,6,6a,9a,10,11,11a-Octahydro-6a-hydroxy-5-(hydroxymethyl)-8,10-dimethyl-11a-(1-methylethenyl)-2-(phenylmethyl)-7H-2,9b-epoxyazuleno[5,4-e]-1,3-benzodioxol-7-one;CHEMBL485800;DTXSID40973441;AKOS040749361;LS-64024;Resiniferonol-9,13,14-orthophenylaectate;(1R,2R,6R,10S,11R,13S,15R,17R)-13-Benzyl-6-hydroxy-8-(hydroxymethyl)-4,17-dimethyl-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-5-one;2-Benzyl-6a-hydroxy-5-(hydroxymethyl)-8,10-dimethyl-11a-(prop-1-en-2-yl)-3a,3b,6,6a,9a,10,11,11a-octahydro-2H,7H-2,9b-epoxyazuleno[4',5':5,6]benzo[1,2-d][1,3]dioxol-7-one

Chemical Property of Ropa

Chemical Property:

• Boiling Point: 638 °C at 760 mmHg
• Flash Point: 213 °C
• PSA: 85.22000
• Density: 1.32 g/cm³
• LogP: 3.23690
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 464.21988874
• Heavy Atom Count: 34
• Complexity: 993

Purity/Quality:

99% ^*data from raw suppliers

Resiniferonol9,13,14-Orthophenylacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2(C3C4C1(C5C=C(C(=O)C5(CC(=C4)CO)O)C)OC(O3)(O2)CC6=CC=CC=C6)C(=C)C
• Isomeric SMILES: C[C@@H]1C[C@]2([C@H]3[C@H]4[C@]1([C@@H]5C=C(C(=O)[C@]5(CC(=C4)CO)O)C)O[C@](O3)(O2)CC6=CC=CC=C6)C(=C)C
• Uses: Resiniferonol 9,13,14-Orthophenylacetate is an analog of Resiniferatoxin (R144670), a transient receptor potential vanilloid-1 (TRPV1) agonist. Labeled Resiniferatoxin has been used to indicate the presence of TRPV1 receptor protein in the brain.

Technology Process of Ropa

There total 38 articles about Ropa 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: 98.0%

C35H36O7 (83117-41-3) → resiniferinol-9,13,14-ortho-phenylacetate (57852-42-3)

Guidance literature:

With barium dihydroxide; In methanol;

DOI:10.1021/ja972279y

Reference yield:

(S)-5-((R)-1-Benzyloxy-allyl)-dihydro-furan-2-one (116386-71-1) → resiniferinol-9,13,14-ortho-phenylacetate (57852-42-3)

Guidance literature:

Multi-step reaction with 37 steps

1.1: LDA / -78 °C

2.1: n-BuLi / tetrahydrofuran / -78 °C

2.2: 98 percent / tetrahydrofuran

3.1: 97 percent / pyridine / CH₂Cl₂ / 0 °C

4.1: 100 percent / NaBH₄ / methanol / 0 °C

5.1: 100 percent / m-chloroperoxybenzoic acid / tetrahydrofuran / 0 °C

6.1: 96 percent / DMAP; pyridine

7.1: 84 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 80 °C

8.1: H₂ / Pd/C / ethyl acetate / 2534.03 Torr

8.2: tetrahydrofuran / Heating

9.1: 98 percent / DMAP; pyridine / 0 °C

10.1: 93 percent / SeO₂; t-BuO₂H / CH₂Cl₂

11.1: 92 percent / MnO₂ / CH₂Cl₂

12.1: 96 percent / CuCN / diethyl ether / -60 °C

13.1: LiBr / tetrahydrofuran / -78 °C

13.2: 33 percent / tetrahydrofuran

14.1: 80 percent / imidazole / CH₂Cl₂

15.1: Cp₂ZrBu₂ / tetrahydrofuran / -78 °C

15.2: 90 percent / AcOH

16.1: 94 percent / NMO / tetrapropylammonium perchlorate / CH₂Cl₂

17.1: 75 percent / tetrahydrofuran / 0 °C

18.1: O₃ / CH₂Cl₂; methanol / -78 °C

18.2: 65 percent / (NH₂)2CS / CH₂Cl₂; methanol / -78 °C

19.1: 99 percent / H₂ / Pd(OH)2/C / ethyl acetate; methanol / 2327.17 Torr

20.1: 97 percent / pyridine / CH₂Cl₂ / 0 °C

21.1: 90 percent / conc. HF / acetonitrile / 0 °C

22.1: pyridine / CH₂Cl₂ / 0 °C

23.1: n-Bu₄NI / acetonitrile

24.1: 92 percent / Rieke Zn / ethanol / Heating

25.1: 61 percent / SeO₂; t-BuO₂H / tetrahydrofuran; hexamethylphosphoric acid triamide / 80 °C

26.1: 88 percent / SOCl₂; propylene oxide / diethyl ether / 0 °C

27.1: 88 percent / AgOBz; 18-crown-6 / acetonitrile

28.1: 73 percent / aq. NaOH / dioxane

29.1: 74 percent / 4-(N,N-dimethylamino)pyridine / toluene

30.1: 46 percent / aq. HClO₄ / methanol

31.1: 48 percent / tetrahydrofuran / -78 °C

32.1: 86 percent / conc. HF / acetonitrile

33.1: 97 percent / pyridine; DMAP / CH₂Cl₂

34.1: 98 percent / DMAP; DABCO / acetonitrile / 110 °C

35.1: NBS / tetrahydrofuran

35.2: Li₂CO₃; LiBr / dimethylformamide / 150 °C

36.1: 98 percent / TBAF / tetrahydrofuran / 0 °C

37.1: 98 percent / Ba(OH)2 / methanol

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; barium dihydroxide; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; selenium(IV) oxide; thionyl chloride; perchloric acid; N-methyl-2-indolinone; 18-crown-6 ether; dibutylbis(cyclopentadienyl)zirconium; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; silver benzoate; tetra-(n-butyl)ammonium iodide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; methyloxirane; lithium bromide; zinc; lithium diisopropyl amide; palladium dihydroxide; palladium on activated charcoal; tetra-n-propylammonium perchlorate; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; acetonitrile; 1.1: Metallation / 1.2: Methylation / 2.1: Metallation / 2.2: Addition / 3.1: Acetylation / 4.1: Reduction / 5.1: Oxidation / 6.1: Acetylation / 7.1: Cycloaddition / 8.1: Hydrogenation / 8.2: Wittig olefination / 9.1: Acetylation / 10.1: Oxidation / 11.1: Oxidation / 12.1: Addition / 13.1: Addition / 13.2: silylation / 14.1: silylation / 15.1: Cyclization / 15.2: acetolysis / 16.1: Oxidation / 17.1: Grignard reaction / 18.1: ozonolysis / 18.2: Reduction / 19.1: Hydrogenolysis / 20.1: Cyclization;

DOI:10.1021/ja972279y

Reference yield:

(3R,5S)-5-((R)-1-Benzyloxy-allyl)-3-methyl-dihydro-furan-2-one (116386-72-2) → resiniferinol-9,13,14-ortho-phenylacetate (57852-42-3)

Guidance literature:

Multi-step reaction with 36 steps

1.1: n-BuLi / tetrahydrofuran / -78 °C

1.2: 98 percent / tetrahydrofuran

2.1: 97 percent / pyridine / CH₂Cl₂ / 0 °C

3.1: 100 percent / NaBH₄ / methanol / 0 °C

4.1: 100 percent / m-chloroperoxybenzoic acid / tetrahydrofuran / 0 °C

5.1: 96 percent / DMAP; pyridine

6.1: 84 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 80 °C

7.1: H₂ / Pd/C / ethyl acetate / 2534.03 Torr

7.2: tetrahydrofuran / Heating

8.1: 98 percent / DMAP; pyridine / 0 °C

9.1: 93 percent / SeO₂; t-BuO₂H / CH₂Cl₂

10.1: 92 percent / MnO₂ / CH₂Cl₂

11.1: 96 percent / CuCN / diethyl ether / -60 °C

12.1: LiBr / tetrahydrofuran / -78 °C

12.2: 33 percent / tetrahydrofuran

13.1: 80 percent / imidazole / CH₂Cl₂

14.1: Cp₂ZrBu₂ / tetrahydrofuran / -78 °C

14.2: 90 percent / AcOH

15.1: 94 percent / NMO / tetrapropylammonium perchlorate / CH₂Cl₂

16.1: 75 percent / tetrahydrofuran / 0 °C

17.1: O₃ / CH₂Cl₂; methanol / -78 °C

17.2: 65 percent / (NH₂)2CS / CH₂Cl₂; methanol / -78 °C

18.1: 99 percent / H₂ / Pd(OH)2/C / ethyl acetate; methanol / 2327.17 Torr

19.1: 97 percent / pyridine / CH₂Cl₂ / 0 °C

20.1: 90 percent / conc. HF / acetonitrile / 0 °C

21.1: pyridine / CH₂Cl₂ / 0 °C

22.1: n-Bu₄NI / acetonitrile

23.1: 92 percent / Rieke Zn / ethanol / Heating

24.1: 61 percent / SeO₂; t-BuO₂H / tetrahydrofuran; hexamethylphosphoric acid triamide / 80 °C

25.1: 88 percent / SOCl₂; propylene oxide / diethyl ether / 0 °C

26.1: 88 percent / AgOBz; 18-crown-6 / acetonitrile

27.1: 73 percent / aq. NaOH / dioxane

28.1: 74 percent / 4-(N,N-dimethylamino)pyridine / toluene

29.1: 46 percent / aq. HClO₄ / methanol

30.1: 48 percent / tetrahydrofuran / -78 °C

31.1: 86 percent / conc. HF / acetonitrile

32.1: 97 percent / pyridine; DMAP / CH₂Cl₂

33.1: 98 percent / DMAP; DABCO / acetonitrile / 110 °C

34.1: NBS / tetrahydrofuran

34.2: Li₂CO₃; LiBr / dimethylformamide / 150 °C

35.1: 98 percent / TBAF / tetrahydrofuran / 0 °C

36.1: 98 percent / Ba(OH)2 / methanol

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; barium dihydroxide; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; selenium(IV) oxide; thionyl chloride; perchloric acid; N-methyl-2-indolinone; 18-crown-6 ether; dibutylbis(cyclopentadienyl)zirconium; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; silver benzoate; tetra-(n-butyl)ammonium iodide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; methyloxirane; lithium bromide; zinc; palladium dihydroxide; palladium on activated charcoal; tetra-n-propylammonium perchlorate; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; acetonitrile; 1.1: Metallation / 1.2: Addition / 2.1: Acetylation / 3.1: Reduction / 4.1: Oxidation / 5.1: Acetylation / 6.1: Cycloaddition / 7.1: Hydrogenation / 7.2: Wittig olefination / 8.1: Acetylation / 9.1: Oxidation / 10.1: Oxidation / 11.1: Addition / 12.1: Addition / 12.2: silylation / 13.1: silylation / 14.1: Cyclization / 14.2: acetolysis / 15.1: Oxidation / 16.1: Grignard reaction / 17.1: ozonolysis / 17.2: Reduction / 18.1: Hydrogenolysis / 19.1: Cyclization / 20.1: desilylation / 21.1: Esterific;

DOI:10.1021/ja972279y

upstream raw materials:

C₃₅H₃₆O₇

(S)-5-((R)-1-Benzyloxy-allyl)-dihydro-furan-2-one

(3R,5S)-5-((R)-1-Benzyloxy-allyl)-3-methyl-dihydro-furan-2-one

(2R,4S,5R)-5-Benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-4-hydroxy-2-methyl-hept-6-en-1-one

Downstream raw materials:

C₃₅H₃₆O₇

C₃₆H₃₃F₅O₇

C₃₆H₃₆F₂O₇

C₃₆H₃₆F₂O₇

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