4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid

Base Information

• Chemical Name: 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid
• CAS No.: 730240-89-8
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 730240-89-8.mol

Synonyms:4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid

Chemical Property of 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid

There total 4 articles about 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid 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: 100.0%

4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester (370884-78-9) → 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid (730240-89-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(01)01205-9

Reference yield:

(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester (250226-93-8) → 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid (730240-89-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / H₂ / 5 percent Pd/C / ethyl acetate / 10 h / 20 °C

2.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

2.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

4.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

With lithium hydroxide; oxalyl dichloride; hydrogen; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; 2.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester (116237-17-3) → 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid (730240-89-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

1.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

3.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

With lithium hydroxide; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; hexane; dichloromethane; water; 1.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)00039-X

upstream raw materials:

4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester

Downstream raw materials:

(2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one

Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl ester

((2R,4aR,9aS)-4a-Methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl)-methanol

(2R,4aR,9aS)-4a-Methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene-6-carboxylic acid methyl ester