(2S,3S,5S)-3-(3,4-dimethoxycinnamyl)-2-(3,4-dimethoxyphenyl)-5-[(S)-(3,4-dimethoxyphenyl)(triisopropylsilyloxy)methyl]tetrahydropyran

Base Information

Chemical Name:(2S,3S,5S)-3-(3,4-dimethoxycinnamyl)-2-(3,4-dimethoxyphenyl)-5-[(S)-(3,4-dimethoxyphenyl)(triisopropylsilyloxy)methyl]tetrahydropyran
CAS No.:934219-80-4
Molecular Formula:C₄₂H₆₀O₈Si
Molecular Weight:721.019
Hs Code.:

Synonyms:(2S,3S,5S)-3-(3,4-dimethoxycinnamyl)-2-(3,4-dimethoxyphenyl)-5-[(S)-(3,4-dimethoxyphenyl)(triisopropylsilyloxy)methyl]tetrahydropyran

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Chemical Property of (2S,3S,5S)-3-(3,4-dimethoxycinnamyl)-2-(3,4-dimethoxyphenyl)-5-[(S)-(3,4-dimethoxyphenyl)(triisopropylsilyloxy)methyl]tetrahydropyran

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Technology Process of (2S,3S,5S)-3-(3,4-dimethoxycinnamyl)-2-(3,4-dimethoxyphenyl)-5-[(S)-(3,4-dimethoxyphenyl)(triisopropylsilyloxy)methyl]tetrahydropyran

There total 17 articles about (2S,3S,5S)-3-(3,4-dimethoxycinnamyl)-2-(3,4-dimethoxyphenyl)-5-[(S)-(3,4-dimethoxyphenyl)(triisopropylsilyloxy)methyl]tetrahydropyran 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: 33.0%

: 934219-79-1
(2S,3S,5S)-3-allyl-2-(3,4-dimethoxyphenyl)-5-[(S)-(3,4-dimethoxyphenyl)(triisopropylsilyloxy)methyl]tetrahydropyran

: 2859-78-1
4-Bromoveratrole

: 934219-80-4
(2S,3S,5S)-3-(3,4-dimethoxycinnamyl)-2-(3,4-dimethoxyphenyl)-5-[(S)-(3,4-dimethoxyphenyl)(triisopropylsilyloxy)methyl]tetrahydropyran

Guidance literature:: With triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 90 ℃; for 6h;
DOI:10.1021/np060461j

Reference yield:

: 934219-70-2
(4S,5S)-5-(3,4-dimethoxyphenyl)-5-(triisopropylsilyloxy)-4-(trityloxymethyl)pentanoic acid

: 934219-80-4
(2S,3S,5S)-3-(3,4-dimethoxycinnamyl)-2-(3,4-dimethoxyphenyl)-5-[(S)-(3,4-dimethoxyphenyl)(triisopropylsilyloxy)methyl]tetrahydropyran

Guidance literature:: Multi-step reaction with 11 steps

1: Et₃N / tetrahydrofuran / 1 h / 0 °C

2: 18.6 g / tetrahydrofuran / 1 h / 0 °C

3: 50 percent / KHMDS / toluene; tetrahydrofuran / 16 h / -70 - 20 °C

4: 89 percent / LiBH₄ / methanol; tetrahydrofuran / 1 h / 20 °C

5: 76 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 16 h / 20 °C

6: 93 percent / tetrahydrofuran / 1 h / 20 °C

7: pyridine / 16 h / 20 °C

8: 38 percent / formic acid / diethyl ether / 0.17 h / -5 °C

9: CH₂Cl₂ / 0.5 h / 0 °C

10: 0.11 g / K₂CO₃ / methanol / 16 h / 20 °C

11: 33 percent / Et₃N / PdCl₂(PPh₃)2 / dimethylformamide / 6 h / 90 °C

With pyridine; lithium borohydride; formic acid; 4 A molecular sieve; potassium hexamethylsilazane; potassium carbonate; triethylamine; pyridinium chlorochromate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 6: Grignard reaction;
DOI:10.1021/np060461j

Reference yield:

: C₄₇H₆₂O₇Si

: 934219-80-4
(2S,3S,5S)-3-(3,4-dimethoxycinnamyl)-2-(3,4-dimethoxyphenyl)-5-[(S)-(3,4-dimethoxyphenyl)(triisopropylsilyloxy)methyl]tetrahydropyran

Guidance literature:: Multi-step reaction with 10 steps

1: 18.6 g / tetrahydrofuran / 1 h / 0 °C

2: 50 percent / KHMDS / toluene; tetrahydrofuran / 16 h / -70 - 20 °C

3: 89 percent / LiBH₄ / methanol; tetrahydrofuran / 1 h / 20 °C

4: 76 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 16 h / 20 °C

5: 93 percent / tetrahydrofuran / 1 h / 20 °C

6: pyridine / 16 h / 20 °C

7: 38 percent / formic acid / diethyl ether / 0.17 h / -5 °C

8: CH₂Cl₂ / 0.5 h / 0 °C

9: 0.11 g / K₂CO₃ / methanol / 16 h / 20 °C

10: 33 percent / Et₃N / PdCl₂(PPh₃)2 / dimethylformamide / 6 h / 90 °C

With pyridine; lithium borohydride; formic acid; 4 A molecular sieve; potassium hexamethylsilazane; potassium carbonate; triethylamine; pyridinium chlorochromate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Grignard reaction;
DOI:10.1021/np060461j