Uvaricin

Base Information

• Chemical Name: Uvaricin
• CAS No.: 82064-83-3
• Molecular Formula: C39H68O7
• Molecular Weight: 648.953
• UNII: YGW6MN47BB
• DSSTox Substance ID: DTXSID501043967
• Nikkaji Number: J2.433.281K
• Wikipedia: Uvaricin
• Wikidata: Q2481797
• ChEMBL ID: CHEMBL504329
• Mol file: 82064-83-3.mol

Synonyms:uvaricin

Chemical Property of Uvaricin

Chemical Property:

• Boiling Point: 730.6°Cat760mmHg
• Flash Point: 211.1°C
• PSA: 91.29000
• Density: 1.026g/cm³
• LogP: 9.45790
• XLogP3: 11.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 27
• Exact Mass: 648.49650450
• Heavy Atom Count: 46
• Complexity: 872

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC(C1CCC(O1)C2CCC(O2)C(CCCCCCCCCCCCC3=CC(OC3=O)C)O)OC(=O)C
• Isomeric SMILES: CCCCCCCCCC[C@@H]([C@H]1CC[C@@H](O1)[C@H]2CC[C@@H](O2)[C@@H](CCCCCCCCCCCCC3=C[C@@H](OC3=O)C)O)OC(=O)C

Technology Process of Uvaricin

There total 37 articles about Uvaricin 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:

undecylaldehyde (112-44-7) → (+)-uvaricin (82064-83-3)

Guidance literature:

Multi-step reaction with 28 steps

1.1: 94 percent / tetrahydrofuran / 0.5 h / 0 °C

2.1: 81 percent / propionic acid / xylene / 2 h / Heating

3.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

4.1: aq. KOH / methanol / 2 h / 60 °C

5.1: 17.2 g / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 20 °C

6.1: 95 percent / diethyl azodicarboxylate; triphenylphosphine / benzene / 16 h / 20 °C

7.1: lithium aluminum hydride / diethyl ether / 2.5 h / 0 °C / Heating

8.1: 6.94 g / p-toluenesulfonic acid / hexane / 16 h / Heating

9.1: 75 percent / Celite; PCC / CH₂Cl₂ / 2 h / 25 °C

10.1: 72 percent / tetrahydrofuran; diethyl ether / 0.5 h / -30 °C

11.1: 91 percent / propionic acid / xylene / 2 h / Heating

12.1: DIBAL-H / toluene / 2 h / -78 °C

13.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

13.2: 4.67 g / toluene; tetrahydrofuran / 16 h / -78 - 25 °C

14.1: 88 percent / DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

15.1: 96 percent / diisopropylethylamine / CH₂Cl₂ / 16 h / 0 - 25 °C

16.1: 63 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

17.1: 99 percent / triethylamine / CH₂Cl₂ / 1 h / -30 - 0 °C

18.1: AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

19.1: p-toluenesulfonic acid / methanol / 16 h / 20 °C

19.2: 13 percent / pyridine / 4 h / 140 °C

20.1: 64 percent / pyridine / 3.5 h / 0 °C

21.1: 90 percent / potassium carbonate / methanol / 16 h / 20 °C

22.1: 69 percent / pyridine / 16 h / 25 °C

23.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 - -30 °C

23.2: BF₃*Et₂O / tetrahydrofuran / 10 h / -78 - -30 °C

24.1: 41 mg / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

25.1: 45 percent / copper(I) iodide / Pd(PPh₃)4 / triethylamine / 22 h / 20 °C

26.1: 62 percent / H₂ / chlorotris(triphenylphosphine)rhodium / benzene; methanol / 16 h / 760 Torr

27.1: m-CPBA / CH₂Cl₂ / 0.33 h / 0 °C

28.1: 2 mg / toluene / 1 h / Heating

With pyridine; potassium hydroxide; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; methanesulfonamide; AD-mix-β; Celite; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; propionic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; triethylamine; toluene; xylene; tert-butyl alcohol; benzene; 1.1: Grignard reaction / 2.1: Claisen-Johnson rearrangement / 3.1: Sharpless dihydroxylation / 4.1: Hydrolysis / 5.1: Cyclization / 6.1: Mitsunobu reaction / 7.1: Reduction / 8.1: Cyclization / 9.1: Oxidation / 10.1: Grignard reaction / 11.1: Claisen-Johnson rearrangement / 12.1: Reduction / 13.1: Metallation / 13.2: Wittig-Horner reaction / 14.1: Reduction / 15.1: Etherification / 16.1: Sharpless dihydroxylation / 17.1: Esterification / 18.1: Sharpless dihydroxylation / 19.1: Hydrolysis / 19.2:;

DOI:10.1021/jo980453a

Reference yield:

(+/-)-tridec-1-en-3-ol (55287-92-8) → (+)-uvaricin (82064-83-3)

Guidance literature:

Multi-step reaction with 27 steps

1.1: 81 percent / propionic acid / xylene / 2 h / Heating

2.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

3.1: aq. KOH / methanol / 2 h / 60 °C

4.1: 17.2 g / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 20 °C

5.1: 95 percent / diethyl azodicarboxylate; triphenylphosphine / benzene / 16 h / 20 °C

6.1: lithium aluminum hydride / diethyl ether / 2.5 h / 0 °C / Heating

7.1: 6.94 g / p-toluenesulfonic acid / hexane / 16 h / Heating

8.1: 75 percent / Celite; PCC / CH₂Cl₂ / 2 h / 25 °C

9.1: 72 percent / tetrahydrofuran; diethyl ether / 0.5 h / -30 °C

10.1: 91 percent / propionic acid / xylene / 2 h / Heating

11.1: DIBAL-H / toluene / 2 h / -78 °C

12.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

12.2: 4.67 g / toluene; tetrahydrofuran / 16 h / -78 - 25 °C

13.1: 88 percent / DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

14.1: 96 percent / diisopropylethylamine / CH₂Cl₂ / 16 h / 0 - 25 °C

15.1: 63 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

16.1: 99 percent / triethylamine / CH₂Cl₂ / 1 h / -30 - 0 °C

17.1: AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

18.1: p-toluenesulfonic acid / methanol / 16 h / 20 °C

18.2: 13 percent / pyridine / 4 h / 140 °C

19.1: 64 percent / pyridine / 3.5 h / 0 °C

20.1: 90 percent / potassium carbonate / methanol / 16 h / 20 °C

21.1: 69 percent / pyridine / 16 h / 25 °C

22.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 - -30 °C

22.2: BF₃*Et₂O / tetrahydrofuran / 10 h / -78 - -30 °C

23.1: 41 mg / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

24.1: 45 percent / copper(I) iodide / Pd(PPh₃)4 / triethylamine / 22 h / 20 °C

25.1: 62 percent / H₂ / chlorotris(triphenylphosphine)rhodium / benzene; methanol / 16 h / 760 Torr

26.1: m-CPBA / CH₂Cl₂ / 0.33 h / 0 °C

27.1: 2 mg / toluene / 1 h / Heating

With pyridine; potassium hydroxide; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; methanesulfonamide; AD-mix-β; Celite; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; propionic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; triethylamine; toluene; xylene; tert-butyl alcohol; benzene; 1.1: Claisen-Johnson rearrangement / 2.1: Sharpless dihydroxylation / 3.1: Hydrolysis / 4.1: Cyclization / 5.1: Mitsunobu reaction / 6.1: Reduction / 7.1: Cyclization / 8.1: Oxidation / 9.1: Grignard reaction / 10.1: Claisen-Johnson rearrangement / 11.1: Reduction / 12.1: Metallation / 12.2: Wittig-Horner reaction / 13.1: Reduction / 14.1: Etherification / 15.1: Sharpless dihydroxylation / 16.1: Esterification / 17.1: Sharpless dihydroxylation / 18.1: Hydrolysis / 18.2: Cyclization / 19.1: Tosyl;

DOI:10.1021/jo980453a

Reference yield:

(E)-pentadec-4-enoic acid ethyl ester (59101-21-2) → (+)-uvaricin (82064-83-3)

Guidance literature:

Multi-step reaction with 26 steps

1.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

2.1: aq. KOH / methanol / 2 h / 60 °C

3.1: 17.2 g / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 20 °C

4.1: 95 percent / diethyl azodicarboxylate; triphenylphosphine / benzene / 16 h / 20 °C

5.1: lithium aluminum hydride / diethyl ether / 2.5 h / 0 °C / Heating

6.1: 6.94 g / p-toluenesulfonic acid / hexane / 16 h / Heating

7.1: 75 percent / Celite; PCC / CH₂Cl₂ / 2 h / 25 °C

8.1: 72 percent / tetrahydrofuran; diethyl ether / 0.5 h / -30 °C

9.1: 91 percent / propionic acid / xylene / 2 h / Heating

10.1: DIBAL-H / toluene / 2 h / -78 °C

11.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

11.2: 4.67 g / toluene; tetrahydrofuran / 16 h / -78 - 25 °C

12.1: 88 percent / DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

13.1: 96 percent / diisopropylethylamine / CH₂Cl₂ / 16 h / 0 - 25 °C

14.1: 63 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

15.1: 99 percent / triethylamine / CH₂Cl₂ / 1 h / -30 - 0 °C

16.1: AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

17.1: p-toluenesulfonic acid / methanol / 16 h / 20 °C

17.2: 13 percent / pyridine / 4 h / 140 °C

18.1: 64 percent / pyridine / 3.5 h / 0 °C

19.1: 90 percent / potassium carbonate / methanol / 16 h / 20 °C

20.1: 69 percent / pyridine / 16 h / 25 °C

21.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 - -30 °C

21.2: BF₃*Et₂O / tetrahydrofuran / 10 h / -78 - -30 °C

22.1: 41 mg / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

23.1: 45 percent / copper(I) iodide / Pd(PPh₃)4 / triethylamine / 22 h / 20 °C

24.1: 62 percent / H₂ / chlorotris(triphenylphosphine)rhodium / benzene; methanol / 16 h / 760 Torr

25.1: m-CPBA / CH₂Cl₂ / 0.33 h / 0 °C

26.1: 2 mg / toluene / 1 h / Heating

With pyridine; potassium hydroxide; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; methanesulfonamide; AD-mix-β; Celite; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; propionic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; triethylamine; toluene; xylene; tert-butyl alcohol; benzene; 1.1: Sharpless dihydroxylation / 2.1: Hydrolysis / 3.1: Cyclization / 4.1: Mitsunobu reaction / 5.1: Reduction / 6.1: Cyclization / 7.1: Oxidation / 8.1: Grignard reaction / 9.1: Claisen-Johnson rearrangement / 10.1: Reduction / 11.1: Metallation / 11.2: Wittig-Horner reaction / 12.1: Reduction / 13.1: Etherification / 14.1: Sharpless dihydroxylation / 15.1: Esterification / 16.1: Sharpless dihydroxylation / 17.1: Hydrolysis / 17.2: Cyclization / 18.1: Tosylation / 19.1: Cyclization / 20.1: Acet;

DOI:10.1021/jo980453a

upstream raw materials:

undecylaldehyde

8-nonyn-1-ol

(+/-)-tridec-1-en-3-ol

(E)-pentadec-4-enoic acid ethyl ester