(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

Base Information

• Chemical Name: (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
• CAS No.: 1571901-08-0
• Molecular Formula: C₂₈H₄₀O₇Si
• Molecular Weight: 516.707

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 22 articles about (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 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: 72.0%

C30H44O8Si (1571901-06-8) → (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 (1571901-08-0)

Guidance literature:

With dimethylsulfide; magnesium bromide ethyl etherate; In diethyl ether; dichloromethane; at 40 ℃; for 6h;

DOI:10.1039/c3ob42367k

Reference yield:

(4R,5R,E)-5-(4-methoxybenzyloxy)hex-2-ene-1,4-diol (1571900-66-7) → (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 (1571901-08-0)

Guidance literature:

Multi-step reaction with 20 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

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; 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

Reference yield:

(R)-(+)-1-(2-furyl)ethanol (27948-61-4) → (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 (1571901-08-0)

Guidance literature:

Multi-step reaction with 23 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C

1.2: 2 h

2.1: N-Bromosuccinimide; sodium hydrogencarbonate / acetone; water / 1.5 h / -15 °C

2.2: 6 h / 20 °C

3.1: cerium(III) chloride heptahydrate / methanol / 0.17 h / -100 °C

3.2: 2 h / -100 °C

4.1: 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C

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

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

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

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

8.2: 0.42 h / 0 °C

9.1: dichloromethane / 6 h / 20 °C

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

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

11.2: Inert atmosphere; Molecular sieve

12.1: 1-methyl-1H-imidazole / toluene / 5 h / 20 °C / Inert atmosphere

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

14.1: 1H-imidazole / N,N-dimethyl-formamide / 9 h / 20 °C

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

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

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

17.2: 2 h / 25 °C

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

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

20.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 16 h / 20 °C

21.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C / pH 7

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

23.1: magnesium bromide ethyl etherate; dimethylsulfide / dichloromethane; diethyl ether / 6 h / 40 °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-Bromosuccinimide; n-butyllithium; oxalyl dichloride; dimethylsulfide; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diethylzinc; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; 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; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; mineral oil; 3.1: |Luche Cerium Reduction / 3.2: |Luche Cerium Reduction / 5.1: |Simmons-Smith Cyclopropanation / 8.1: |Swern Oxidation / 8.2: |Swern Oxidation / 9.1: |Wittig Olefination / 18.1: |Steglich Esterification / 22.1: |Mitsunobu Displacement;

DOI:10.1039/c3ob42367k

upstream raw materials:

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

(4R,5R,E)-5-(4-methoxybenzyloxy)hex-2-ene-1,4-diol

(R)-(+)-1-(2-furyl)ethanol

tert-butyl(((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1(methoxymethoxy)propyl)cyclopropyl)methoxy)dimethylsilane

Downstream raw materials:

(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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