3-(phenylthio)uvaricin

Base Information

• Chemical Name: 3-(phenylthio)uvaricin
• CAS No.: 213328-48-4
• Molecular Formula: C₄₅H₇₄O₇S
• Molecular Weight: 759.144

Synonyms:3-(phenylthio)uvaricin

Chemical Property of 3-(phenylthio)uvaricin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of 3-(phenylthio)uvaricin

There total 35 articles about 3-(phenylthio)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: 62.0%

3-(phenylthio)-11,12,13,13,14,14-hexadehydrouvaricin → 3-(phenylthio)uvaricin (213328-48-4)

Guidance literature:

With hydrogen; Wilkinson's catalyst; In methanol; benzene; for 16h; under 760 Torr;

DOI:10.1021/jo980453a

Reference yield:

(+/-)-tridec-1-en-3-ol (55287-92-8) → 3-(phenylthio)uvaricin (213328-48-4)

Guidance literature:

Multi-step reaction with 25 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

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; 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:

undecylaldehyde (112-44-7) → 3-(phenylthio)uvaricin (213328-48-4)

Guidance literature:

Multi-step reaction with 26 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

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; 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

upstream raw materials:

undecylaldehyde

8-nonyn-1-ol

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

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

Downstream raw materials:

(+)-uvaricin

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