(1EZ,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-16-oxabicyclo[13.2.2]nonadeca-1,3,8,10-17,18-dione

Base Information

• Chemical Name: (1EZ,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-16-oxabicyclo[13.2.2]nonadeca-1,3,8,10-17,18-dione
• CAS No.: 640270-54-8
• Molecular Formula: C₂₇H₃₂O₆
• Molecular Weight: 452.547

Synonyms:(1EZ,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-16-oxabicyclo[13.2.2]nonadeca-1,3,8,10-17,18-dione

Chemical Property of (1EZ,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-16-oxabicyclo[13.2.2]nonadeca-1,3,8,10-17,18-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1EZ,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-16-oxabicyclo[13.2.2]nonadeca-1,3,8,10-17,18-dione

There total 15 articles about (1EZ,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-16-oxabicyclo[13.2.2]nonadeca-1,3,8,10-17,18-dione 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:

(2R)-1-cyano-2-hydroxy-4-pentyne (182681-88-5) → (1EZ,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-16-oxabicyclo[13.2.2]nonadeca-1,3,8,10-17,18-dione (640270-54-8)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 5.62 g / imidazole / dimethylformamide / 13.5 h / 20 °C

2.1: 100 percent / Dibal-H / toluene / 2 h / -52 °C

3.1: 73 percent / BF₃*Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 6.5 h / 0 °C

5.1: 7.95 g / aq. HF / acetonitrile / 8 h / 20 °C

6.1: Et₂BOMe / tetrahydrofuran; methanol / 0.5 h / -78 °C

6.2: 100 percent / NaBH₄ / tetrahydrofuran; methanol / 8 h / -78 °C

7.1: 93 percent / imidazole / dimethylformamide / 5 h / 20 °C

8.1: 97 percent / AgNO₃; NBS / acetone / 0.5 h / 20 °C

9.1: Pd₂(dba)3; PPh₃; Bu₃SnH / tetrahydrofuran / 2 h / 20 °C

9.2: 84 percent / I₂ / CH₂Cl₂ / 1 h / 20 °C

10.1: 97 percent / CuCl; Pd(PPh₃)4 / tetrahydrofuran; dimethylsulfoxide / 1 h / 20 °C

11.1: 94 percent / NH₄F / methanol / 24 h / 20 °C

12.1: 100 percent / pyridine / 2 h / 20 °C

13.1: 98 percent / toluene; methanol / 3 h / 110 °C

14.1: 84 percent / Pd(PPh₃)4; 1,2-bis(diphenylphosphino)ethane / tetrahydrofuran / 21 h / 20 °C

15.1: HF-pyridine complex; pyridine / 30 h / 20 °C

16.1: iPr₂NEt / methanol / 24 h / 20 °C

17.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

17.2: 55.7 mg / CH₂Cl₂ / 1 h / -78 °C

18.1: 118 mg / mCPBA / CH₂Cl₂ / 3.5 h / -50 °C

With pyridine; 1H-imidazole; ammonium fluoride; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,2-bis-(diphenylphosphino)ethane; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 3.1: Mukaiyama aldol reaction / 10.1: Stille coupling;

DOI:10.1021/ja038732p

Reference yield:

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}hex-5-ynal (640270-59-3) → (1EZ,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-16-oxabicyclo[13.2.2]nonadeca-1,3,8,10-17,18-dione (640270-54-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 73 percent / BF₃*Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

2.1: Dess-Martin periodinane / CH₂Cl₂ / 6.5 h / 0 °C

3.1: 7.95 g / aq. HF / acetonitrile / 8 h / 20 °C

4.1: Et₂BOMe / tetrahydrofuran; methanol / 0.5 h / -78 °C

4.2: 100 percent / NaBH₄ / tetrahydrofuran; methanol / 8 h / -78 °C

5.1: 93 percent / imidazole / dimethylformamide / 5 h / 20 °C

6.1: 97 percent / AgNO₃; NBS / acetone / 0.5 h / 20 °C

7.1: Pd₂(dba)3; PPh₃; Bu₃SnH / tetrahydrofuran / 2 h / 20 °C

7.2: 84 percent / I₂ / CH₂Cl₂ / 1 h / 20 °C

8.1: 97 percent / CuCl; Pd(PPh₃)4 / tetrahydrofuran; dimethylsulfoxide / 1 h / 20 °C

9.1: 94 percent / NH₄F / methanol / 24 h / 20 °C

10.1: 100 percent / pyridine / 2 h / 20 °C

11.1: 98 percent / toluene; methanol / 3 h / 110 °C

12.1: 84 percent / Pd(PPh₃)4; 1,2-bis(diphenylphosphino)ethane / tetrahydrofuran / 21 h / 20 °C

13.1: HF-pyridine complex; pyridine / 30 h / 20 °C

14.1: iPr₂NEt / methanol / 24 h / 20 °C

15.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

15.2: 55.7 mg / CH₂Cl₂ / 1 h / -78 °C

16.1: 118 mg / mCPBA / CH₂Cl₂ / 3.5 h / -50 °C

With pyridine; 1H-imidazole; ammonium fluoride; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; Dess-Martin periodane; pyridine hydrogenfluoride; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,2-bis-(diphenylphosphino)ethane; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: Mukaiyama aldol reaction / 8.1: Stille coupling;

DOI:10.1021/ja038732p

Reference yield:

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}hex-5-ynenitrile (640270-65-1) → (1EZ,3E,6R,7S,8Z,10E,13R,15R)-13-hydroxy-7-[(4-methoxyphenyl)methoxy]-6-methyl-16-oxabicyclo[13.2.2]nonadeca-1,3,8,10-17,18-dione (640270-54-8)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 100 percent / Dibal-H / toluene / 2 h / -52 °C

2.1: 73 percent / BF₃*Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 6.5 h / 0 °C

4.1: 7.95 g / aq. HF / acetonitrile / 8 h / 20 °C

5.1: Et₂BOMe / tetrahydrofuran; methanol / 0.5 h / -78 °C

5.2: 100 percent / NaBH₄ / tetrahydrofuran; methanol / 8 h / -78 °C

6.1: 93 percent / imidazole / dimethylformamide / 5 h / 20 °C

7.1: 97 percent / AgNO₃; NBS / acetone / 0.5 h / 20 °C

8.1: Pd₂(dba)3; PPh₃; Bu₃SnH / tetrahydrofuran / 2 h / 20 °C

8.2: 84 percent / I₂ / CH₂Cl₂ / 1 h / 20 °C

9.1: 97 percent / CuCl; Pd(PPh₃)4 / tetrahydrofuran; dimethylsulfoxide / 1 h / 20 °C

10.1: 94 percent / NH₄F / methanol / 24 h / 20 °C

11.1: 100 percent / pyridine / 2 h / 20 °C

12.1: 98 percent / toluene; methanol / 3 h / 110 °C

13.1: 84 percent / Pd(PPh₃)4; 1,2-bis(diphenylphosphino)ethane / tetrahydrofuran / 21 h / 20 °C

14.1: HF-pyridine complex; pyridine / 30 h / 20 °C

15.1: iPr₂NEt / methanol / 24 h / 20 °C

16.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

16.2: 55.7 mg / CH₂Cl₂ / 1 h / -78 °C

17.1: 118 mg / mCPBA / CH₂Cl₂ / 3.5 h / -50 °C

With pyridine; 1H-imidazole; ammonium fluoride; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,2-bis-(diphenylphosphino)ethane; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 2.1: Mukaiyama aldol reaction / 9.1: Stille coupling;

DOI:10.1021/ja038732p

upstream raw materials:

(2R)-1-cyano-2-hydroxy-4-pentyne

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}hex-5-ynal

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}hex-5-ynenitrile

(2R,4R)-1-(2,2-dimethyl-1,3-dioxin-4-one-6-yl)-6-heptyne-2,4-diol

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