(R)-2-[(4R,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propionaldehyde

Base Information

• Chemical Name: (R)-2-[(4R,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propionaldehyde
• CAS No.: 383187-80-2
• Molecular Formula: C₂₀H₃₀O₆
• Molecular Weight: 366.455

Synonyms:(R)-2-[(4R,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propionaldehyde

Chemical Property of (R)-2-[(4R,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propionaldehyde

Chemical Property:

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Technology Process of (R)-2-[(4R,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propionaldehyde

There total 12 articles about (R)-2-[(4R,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propionaldehyde 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:

(S)-2-[(4S,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propan-1-ol (383187-73-3) → (R)-2-[(4R,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propionaldehyde (383187-80-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1.75h;

DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W

Reference yield:

2,6-dimethoxytoluene (5673-07-4) → (R)-2-[(4R,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propionaldehyde (383187-80-2)

Guidance literature:

Multi-step reaction with 9 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

6.1: Me₄NBH(OAc)3 / acetonitrile; acetic acid / 16 h / -30 - 20 °C

7.1: 93 percent / 18 h / 20 °C

8.1: 83 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂; H₂O; various solvent(s) / 0.5 h

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.75 h / -78 - 0 °C

With boron trifluoride dimethyl etherate; oxalyl dichloride; 4 A molecular sieve; titanium tetrachloride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; water; acetic acid; acetone; acetonitrile; benzene; 1.1: Friedel-Crafts acylation / 2.1: Bayer-Villiger oxidation / 3.1: ortho-Fries rearrangement / 9.1: Swern oxidation;

DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W

Reference yield:

2',4'-dimethoxy-3'-methylpropiophenone (77942-13-3) → (R)-2-[(4R,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propionaldehyde (383187-80-2)

Guidance literature:

Multi-step reaction with 8 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

5.1: Me₄NBH(OAc)3 / acetonitrile; acetic acid / 16 h / -30 - 20 °C

6.1: 93 percent / 18 h / 20 °C

7.1: 83 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂; H₂O; various solvent(s) / 0.5 h

8.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.75 h / -78 - 0 °C

With boron trifluoride dimethyl etherate; oxalyl dichloride; 4 A molecular sieve; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; water; acetic acid; acetone; acetonitrile; 1.1: Bayer-Villiger oxidation / 2.1: ortho-Fries rearrangement / 8.1: Swern oxidation;

DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W

upstream raw materials:

(S)-2-[(4S,5R,6R)-2,2,5-Trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-propan-1-ol

2,6-dimethoxytoluene

2',4'-dimethoxy-3'-methylpropiophenone

1-bromo-2,3,5-trimethoxy-4-methylbenzaldehyde

Downstream raw materials:

(2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol

(R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-[(2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-yl]-3-methyl-butan-2-one

(E)-(2R,6S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-6-[(4S,5R,6R)-2,2,5-trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-hept-4-en-3-one

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