(1R,4S)-4-(acetyloxy)-4-{(2R,5R)-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyltetrahydrofuran-2-yl}-1-{(2S,5R)-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyltetrahydrofuran-2-yl}butyl acetate

Base Information

• Chemical Name: (1R,4S)-4-(acetyloxy)-4-{(2R,5R)-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyltetrahydrofuran-2-yl}-1-{(2S,5R)-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyltetrahydrofuran-2-yl}butyl acetate
• CAS No.: 134856-96-5
• Molecular Formula: C34H58O8
• Molecular Weight: 594.8195

Synonyms:

Chemical Property of (1R,4S)-4-(acetyloxy)-4-{(2R,5R)-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyltetrahydrofuran-2-yl}-1-{(2S,5R)-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyltetrahydrofuran-2-yl}butyl acetate

Chemical Property:

• Vapor Pressure: 4.91E-20mmHg at 25°C
• Boiling Point: 656.7°Cat760mmHg
• Flash Point: 192.8°C
• Density: 1.065g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,4S)-4-(acetyloxy)-4-{(2R,5R)-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyltetrahydrofuran-2-yl}-1-{(2S,5R)-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyltetrahydrofuran-2-yl}butyl acetate

There total 58 articles about (1R,4S)-4-(acetyloxy)-4-{(2R,5R)-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyltetrahydrofuran-2-yl}-1-{(2S,5R)-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyltetrahydrofuran-2-yl}butyl acetate 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: 80.0%

acetic anhydride (108-24-7) + 14-deacetyl eurylene (134856-97-6) → (+)-eurylene (134856-96-5)

Guidance literature:

With pyridine; at 20 ℃; for 40h;

Reference yield:

(2E,6E)-2,7-dimethylocta-2,6-diene-1,8-diol (32663-39-1) → (+)-eurylene (134856-96-5)

Guidance literature:

Multi-step reaction with 18 steps

1: 55 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

2: 83 percent / tBuOOH; Ti(OiPr)4; molecular sieves 4 Angstroem / diethyl D-tartrate / CH₂Cl₂ / 2 h / -20 °C

3: 83 percent / Ti(OiPr)4 / benzene / 2 h / 0 °C

4: 88 percent / CSA / CH₂Cl₂ / 2 h / 0 °C

5: 99 percent / Bu₄NF / tetrahydrofuran / 3 h / 20 °C

6: 89 percent / tBuOOH; Ti(OiPr)4; molecular sieves 4 Angstroem / diethyl L-tartrate / CH₂Cl₂ / 3 h / -20 °C

7: Ti(OMPM)4 / benzene / 12 h / 60 °C

8: aq. AcOH / 5 h / 20 °C

9: pyridine / CH₂Cl₂ / 5 h / 0 - 20 °C

10: K₂CO₃ / methanol / 1 h / 20 °C

11: TMEDA / tetrahydrofuran / 2.5 h / -78 - 0 °C

12: Na; iPrOH / tetrahydrofuran / 15 h / Heating

13: 91 percent / pyridine / 12 h / 20 °C

14: 68 percent / DDQ; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 0 °C

15: 89 percent / aq. AcOH / 16 h / 20 °C

16: 84 percent / TFAA; [(CF₃CO₂)ReO₃*2CH₃CN] / CH₂Cl₂; acetonitrile / 1.5 h / -40 °C

17: 47 percent / PCC / CH₂Cl₂ / 0.5 h / 20 °C

18: 80 percent / pyridine / 40 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,-tetramethylethylenediamine; [(CF₃CO₂)ReO₃*2CH₃CN]; Ti(OMPM)4; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium; potassium carbonate; acetic acid; isopropyl alcohol; pyridinium chlorochromate; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene;

Reference yield:

(2E,6E)-8-tert-butyldimethylsilyloxy-2,7-dimethyl-2,6-octadien-1-ol (294623-80-6) → (+)-eurylene (134856-96-5)

Guidance literature:

Multi-step reaction with 17 steps

1: 83 percent / tBuOOH; Ti(OiPr)4; molecular sieves 4 Angstroem / diethyl D-tartrate / CH₂Cl₂ / 2 h / -20 °C

2: 83 percent / Ti(OiPr)4 / benzene / 2 h / 0 °C

3: 88 percent / CSA / CH₂Cl₂ / 2 h / 0 °C

4: 99 percent / Bu₄NF / tetrahydrofuran / 3 h / 20 °C

5: 89 percent / tBuOOH; Ti(OiPr)4; molecular sieves 4 Angstroem / diethyl L-tartrate / CH₂Cl₂ / 3 h / -20 °C

6: Ti(OMPM)4 / benzene / 12 h / 60 °C

7: aq. AcOH / 5 h / 20 °C

8: pyridine / CH₂Cl₂ / 5 h / 0 - 20 °C

9: K₂CO₃ / methanol / 1 h / 20 °C

10: TMEDA / tetrahydrofuran / 2.5 h / -78 - 0 °C

11: Na; iPrOH / tetrahydrofuran / 15 h / Heating

12: 91 percent / pyridine / 12 h / 20 °C

13: 68 percent / DDQ; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 0 °C

14: 89 percent / aq. AcOH / 16 h / 20 °C

15: 84 percent / TFAA; [(CF₃CO₂)ReO₃*2CH₃CN] / CH₂Cl₂; acetonitrile / 1.5 h / -40 °C

16: 47 percent / PCC / CH₂Cl₂ / 0.5 h / 20 °C

17: 80 percent / pyridine / 40 h / 20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,-tetramethylethylenediamine; [(CF₃CO₂)ReO₃*2CH₃CN]; Ti(OMPM)4; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium; potassium carbonate; acetic acid; isopropyl alcohol; pyridinium chlorochromate; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene;

upstream raw materials:

acetic anhydride

11,14-dideacetylated eurylene

14-deacetyl eurylene

3-methyl-2-butenylmagnesium chloride

Refernces

Enantioselective formal synthesis of eurylene: Synthesis of the cis - And trans -THF fragments using oxidative cyclization

10.1021/ol100513y

The research describes a formal synthesis of eurylene, a squalenoid natural product with cytotoxic properties, focusing on the preparation of both cis- and trans-tetrahydrofuran (THF) fragments using oxidative cyclization. The study aimed to develop a method to synthesize the complex structure of eurylene, which contains two nonadjacently linked THF diol systems with a total of eight stereogenic centers. The researchers utilized permanganate-mediated oxidative monocyclizations of trienes to generate the cis- and trans-THF fragments while retaining the electron-rich trisubstituted alkenes. The study concluded that the permanganate-mediated oxidative cyclization could be adapted to selectively produce both cis- and trans-THF diols, with the trans-THF diol motif being synthesized from a cis-THF diol precursor through a deoxygenation process. This work represents the first reported application of permanganate-mediated oxidative cyclization to the synthesis of a trans-THF system, offering a new approach to constructing complex natural product architectures.

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