Acetic acid (1S,4R)-4-[(2S,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-1-[(2R,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-4-(4-methoxy-benzyloxy)-butyl ester

Base Information

• Chemical Name: Acetic acid (1S,4R)-4-[(2S,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-1-[(2R,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-4-(4-methoxy-benzyloxy)-butyl ester
• CAS No.: 678999-08-1
• Molecular Formula: C₄₀H₆₄O₈
• Molecular Weight: 672.943

Synonyms:

Chemical Property of Acetic acid (1S,4R)-4-[(2S,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-1-[(2R,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-4-(4-methoxy-benzyloxy)-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Acetic acid (1S,4R)-4-[(2S,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-1-[(2R,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-4-(4-methoxy-benzyloxy)-butyl ester

There total 27 articles about Acetic acid (1S,4R)-4-[(2S,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-1-[(2R,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-4-(4-methoxy-benzyloxy)-butyl ester 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:

3-methyl-2-butenylmagnesium chloride (35189-96-9) → Acetic acid (1S,4R)-4-[(2S,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-1-[(2R,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-4-(4-methoxy-benzyloxy)-butyl ester (678999-08-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 70 percent / CuI / tetrahydrofuran / 0.5 h / -15 °C

2: 87 percent / aq. p-TsOH / ethanol / 2 h / 50 °C

3: 82 percent / pyridine / 1 h / 0 °C

4: 92 percent / K₂CO₃ / methanol / 0.33 h / 0 °C

5: 100 percent / n-BuLi; DMPU / tetrahydrofuran; hexane / 5 h / -78 - -25 °C

6: 78 percent / NaH / dimethylformamide / 3 h / 0 °C

7: 100 percent / imidazole / dimethylformamide / 0.17 h / 0 °C

8: 94 percent / DMPU; LHMDS / tetrahydrofuran; hexane / 3 h / -78 - -25 °C

9: 98 percent / SmI₂; MeOH / tetrahydrofuran / 0.17 h / -78 °C

10: 99 percent / aq. HCl / methanol / 0.17 h / 20 °C

11: 95 percent / NaBH₄ / methanol / 0.17 h / 0 °C

12: 25 mg / pyridine / 17 h / 50 °C

With pyridine; 1H-imidazole; hydrogenchloride; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; samarium diiodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide;

DOI:10.1021/ol036471i

Reference yield:

(E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-1,6-dien-3-ol (158512-40-4) → Acetic acid (1S,4R)-4-[(2S,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-1-[(2R,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-4-(4-methoxy-benzyloxy)-butyl ester (678999-08-1)

Guidance literature:

Multi-step reaction with 17 steps

1: 90 percent / VO(acac)2; TBHP / benzene; H₂O / 0.33 h / 20 °C

2: m-CPBA / CH₂Cl₂ / 3 h / 0 °C

3: 5.100 g / silica gel / 48 h

4: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

5: 91 percent / PPTS / CH₂Cl₂ / 7 h / 20 °C

6: 70 percent / CuI / tetrahydrofuran / 0.5 h / -15 °C

7: 87 percent / aq. p-TsOH / ethanol / 2 h / 50 °C

8: 82 percent / pyridine / 1 h / 0 °C

9: 92 percent / K₂CO₃ / methanol / 0.33 h / 0 °C

10: 100 percent / n-BuLi; DMPU / tetrahydrofuran; hexane / 5 h / -78 - -25 °C

11: 78 percent / NaH / dimethylformamide / 3 h / 0 °C

12: 100 percent / imidazole / dimethylformamide / 0.17 h / 0 °C

13: 94 percent / DMPU; LHMDS / tetrahydrofuran; hexane / 3 h / -78 - -25 °C

14: 98 percent / SmI₂; MeOH / tetrahydrofuran / 0.17 h / -78 °C

15: 99 percent / aq. HCl / methanol / 0.17 h / 20 °C

16: 95 percent / NaBH₄ / methanol / 0.17 h / 0 °C

17: 25 mg / pyridine / 17 h / 50 °C

With pyridine; 1H-imidazole; hydrogenchloride; methanol; tert.-butylhydroperoxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; samarium diiodide; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silica gel; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ol036471i

Reference yield:

(E)-(R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-1-((S)-2-methyl-oxiranyl)-hex-4-en-1-ol (158389-04-9) → Acetic acid (1S,4R)-4-[(2S,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-1-[(2R,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-4-(4-methoxy-benzyloxy)-butyl ester (678999-08-1)

Guidance literature:

Multi-step reaction with 16 steps

1: m-CPBA / CH₂Cl₂ / 3 h / 0 °C

2: 5.100 g / silica gel / 48 h

3: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

4: 91 percent / PPTS / CH₂Cl₂ / 7 h / 20 °C

5: 70 percent / CuI / tetrahydrofuran / 0.5 h / -15 °C

6: 87 percent / aq. p-TsOH / ethanol / 2 h / 50 °C

7: 82 percent / pyridine / 1 h / 0 °C

8: 92 percent / K₂CO₃ / methanol / 0.33 h / 0 °C

9: 100 percent / n-BuLi; DMPU / tetrahydrofuran; hexane / 5 h / -78 - -25 °C

10: 78 percent / NaH / dimethylformamide / 3 h / 0 °C

11: 100 percent / imidazole / dimethylformamide / 0.17 h / 0 °C

12: 94 percent / DMPU; LHMDS / tetrahydrofuran; hexane / 3 h / -78 - -25 °C

13: 98 percent / SmI₂; MeOH / tetrahydrofuran / 0.17 h / -78 °C

14: 99 percent / aq. HCl / methanol / 0.17 h / 20 °C

15: 95 percent / NaBH₄ / methanol / 0.17 h / 0 °C

16: 25 mg / pyridine / 17 h / 50 °C

With pyridine; 1H-imidazole; hydrogenchloride; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; samarium diiodide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silica gel; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol036471i

upstream raw materials:

acetic anhydride

(S)-2-{(2R,5S)-5-[(R)-4-Hydroxy-4-[(2R,5R)-5-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-1-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-furan-2-yl}-6-methyl-hept-5-en-2-ol

3-methyl-2-butenylmagnesium chloride

(S)-2-[(2R,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-methyl-tetrahydro-furan-2-yl]-6-methyl-hept-5-en-2-ol

Downstream raw materials:

(+)-eurylene

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