(E)-((1R,2R)-1-hydroxy-1-((1S,2S)-2-((S)-hydroxy((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)propan-2-yl) 3-(4-methoxyphenyl)acrylate

Base Information

Chemical Name:(E)-((1R,2R)-1-hydroxy-1-((1S,2S)-2-((S)-hydroxy((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)propan-2-yl) 3-(4-methoxyphenyl)acrylate
CAS No.:1571901-10-4
Molecular Formula:C₂₂H₂₆O₇
Molecular Weight:402.444
Hs Code.:

Synonyms:(E)-((1R,2R)-1-hydroxy-1-((1S,2S)-2-((S)-hydroxy((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)propan-2-yl) 3-(4-methoxyphenyl)acrylate

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Chemical Property of (E)-((1R,2R)-1-hydroxy-1-((1S,2S)-2-((S)-hydroxy((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)propan-2-yl) 3-(4-methoxyphenyl)acrylate

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Technology Process of (E)-((1R,2R)-1-hydroxy-1-((1S,2S)-2-((S)-hydroxy((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)propan-2-yl) 3-(4-methoxyphenyl)acrylate

There total 22 articles about (E)-((1R,2R)-1-hydroxy-1-((1S,2S)-2-((S)-hydroxy((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)propan-2-yl) 3-(4-methoxyphenyl)acrylate 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: 85.0%

: 1571901-08-0
(E)-((1R,2R)-1-((1S,2S)-2-((S)-(tert-butyldimethylsilyloxy)((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)-1-hydroxypropan-2-yl) 3-(4-methoxyphenyl)acrylate

: 1571901-10-4
(E)-((1R,2R)-1-hydroxy-1-((1S,2S)-2-((S)-hydroxy((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)propan-2-yl) 3-(4-methoxyphenyl)acrylate

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 6h;
DOI:10.1039/c3ob42367k

Reference yield:

: 1571900-72-5
(2R,3R,E)-6-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)hex-4-en-3-ol

: 1571901-10-4
(E)-((1R,2R)-1-hydroxy-1-((1S,2S)-2-((S)-hydroxy((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)propan-2-yl) 3-(4-methoxyphenyl)acrylate

Guidance literature:: Multi-step reaction with 20 steps

1.1: diethylzinc / dichloromethane; hexane / -78 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h

4.2: 0.42 h / 0 °C

5.1: dichloromethane / 6 h / 20 °C

6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C

7.1: titanium(IV) isopropylate / dichloromethane / 0.5 h / Inert atmosphere; Molecular sieve

7.2: Inert atmosphere; Molecular sieve

8.1: 1-methyl-1H-imidazole / toluene / 5 h / 20 °C / Inert atmosphere

9.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

10.1: 1H-imidazole / N,N-dimethyl-formamide / 9 h / 20 °C

11.1: methanol; potassium carbonate / 12 h / 20 °C

12.1: N-tosylimidazole; sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C

13.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -15 °C

13.2: 2 h / 25 °C

14.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 20 °C

15.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / Reflux

16.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 16 h / 20 °C

17.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C / pH 7

18.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 20 °C

19.1: magnesium bromide ethyl etherate; dimethylsulfide / dichloromethane; diethyl ether / 6 h / 40 °C

20.1: pyridine hydrogenfluoride / tetrahydrofuran / 6 h / 20 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 1-methyl-1H-imidazole; titanium(IV) isopropylate; methanol; dmap; n-butyllithium; oxalyl dichloride; dimethylsulfide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diethylzinc; sodium hydride; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; magnesium bromide ethyl etherate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; N-tosylimidazole; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 1.1: |Simmons-Smith Cyclopropanation / 4.1: |Swern Oxidation / 4.2: |Swern Oxidation / 5.1: |Wittig Olefination / 14.1: |Steglich Esterification / 18.1: |Mitsunobu Displacement;
DOI:10.1039/c3ob42367k

Reference yield:

: 1571900-66-7
(4R,5R,E)-5-(4-methoxybenzyloxy)hex-2-ene-1,4-diol

: 1571901-10-4
(E)-((1R,2R)-1-hydroxy-1-((1S,2S)-2-((S)-hydroxy((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)propan-2-yl) 3-(4-methoxyphenyl)acrylate

Guidance literature:: Multi-step reaction with 21 steps

1.1: 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C

2.1: diethylzinc / dichloromethane; hexane / -78 - 20 °C

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h

5.2: 0.42 h / 0 °C

6.1: dichloromethane / 6 h / 20 °C

7.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C

8.1: titanium(IV) isopropylate / dichloromethane / 0.5 h / Inert atmosphere; Molecular sieve

8.2: Inert atmosphere; Molecular sieve

9.1: 1-methyl-1H-imidazole / toluene / 5 h / 20 °C / Inert atmosphere

10.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

11.1: 1H-imidazole / N,N-dimethyl-formamide / 9 h / 20 °C

12.1: methanol; potassium carbonate / 12 h / 20 °C

13.1: N-tosylimidazole; sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C

14.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -15 °C

14.2: 2 h / 25 °C

15.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 20 °C

16.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / Reflux

17.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 16 h / 20 °C

18.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C / pH 7

19.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 20 °C

20.1: magnesium bromide ethyl etherate; dimethylsulfide / dichloromethane; diethyl ether / 6 h / 40 °C

21.1: pyridine hydrogenfluoride / tetrahydrofuran / 6 h / 20 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 1-methyl-1H-imidazole; titanium(IV) isopropylate; methanol; dmap; n-butyllithium; oxalyl dichloride; dimethylsulfide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diethylzinc; sodium hydride; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; magnesium bromide ethyl etherate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; N-tosylimidazole; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 2.1: |Simmons-Smith Cyclopropanation / 5.1: |Swern Oxidation / 5.2: |Swern Oxidation / 6.1: |Wittig Olefination / 15.1: |Steglich Esterification / 19.1: |Mitsunobu Displacement;
DOI:10.1039/c3ob42367k