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

Base Information

• Chemical Name: 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester
• CAS No.: 370884-78-9
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.348
• Mol file: 370884-78-9.mol

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

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

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 methyl ester

There total 4 articles about 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester 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: 70.0%

trimethylaluminum (75-24-1) + 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 methyl ester (370884-78-9)

Guidance literature:

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester; With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

trimethylaluminum; In dichloromethane; 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 methyl ester (370884-78-9)

Guidance literature:

Multi-step reaction with 3 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

With oxalyl dichloride; hydrogen; dimethyl sulfoxide; palladium on activated charcoal; In hexane; dichloromethane; 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 methyl ester (370884-78-9)

Guidance literature:

Multi-step reaction with 2 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

With oxalyl dichloride; dimethyl sulfoxide; In hexane; dichloromethane; 1.1: Swern oxidation;

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

upstream raw materials:

trimethylaluminum

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:

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

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-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one

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