(2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one

Base Information

Chemical Name:(2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one
CAS No.:383187-47-1
Molecular Formula:C₂₅H₃₄O₇
Molecular Weight:446.541
Hs Code.:

Synonyms:(2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one

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Chemical Property of (2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one

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Technology Process of (2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one

There total 5 articles about (2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one 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: 58.0%

: 132969-60-9
(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal

: 383187-40-4
1-(2,3,5-trimethoxy-4-methyl-phenyl)-propan-1-one

: 383187-47-1
(2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one

Guidance literature:: 1-(2,3,5-trimethoxy-4-methyl-phenyl)-propan-1-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.75h;

With triisopropoxytitanium(IV) chloride; In tetrahydrofuran; at -78 - -40 ℃; for 1h;

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal; In tetrahydrofuran; at -78 - -40 ℃; for 3h;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W

Reference yield:

: 5673-07-4
2,6-dimethoxytoluene

: 383187-47-1
(2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / TiCl₄ / benzene / 0.5 h / 0 °C

2.1: 85 percent / mCPBA / CH₂Cl₂ / 20 °C

3.1: 76 percent / BF₃OMe₂ / 3 h / 90 °C

4.1: 99 percent / K₂CO₃ / acetone / 40 h / 20 °C

5.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C

5.2: Ti(i-PrO)3Cl / tetrahydrofuran / 1 h / -78 - -40 °C

5.3: 58 percent / tetrahydrofuran / 3 h / -78 - -40 °C

With boron trifluoride dimethyl etherate; titanium tetrachloride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetone; benzene; 1.1: Friedel-Crafts acylation / 2.1: Bayer-Villiger oxidation / 3.1: ortho-Fries rearrangement;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W

Reference yield:

: 77942-13-3
2',4'-dimethoxy-3'-methylpropiophenone

: 383187-47-1
(2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / mCPBA / CH₂Cl₂ / 20 °C

2.1: 76 percent / BF₃OMe₂ / 3 h / 90 °C

3.1: 99 percent / K₂CO₃ / acetone / 40 h / 20 °C

4.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C

4.2: Ti(i-PrO)3Cl / tetrahydrofuran / 1 h / -78 - -40 °C

4.3: 58 percent / tetrahydrofuran / 3 h / -78 - -40 °C

With boron trifluoride dimethyl etherate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetone; 1.1: Bayer-Villiger oxidation / 2.1: ortho-Fries rearrangement;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W