3-Hydroxy-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-hex-5-enoic acid tert-butyl ester

Base Information

• Chemical Name: 3-Hydroxy-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-hex-5-enoic acid tert-butyl ester
• CAS No.: 330954-55-7
• Molecular Formula: C₂₃H₃₂O₇
• Molecular Weight: 420.503
• Mol file: 330954-55-7.mol

Synonyms:3-Hydroxy-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-hex-5-enoic acid tert-butyl ester

Chemical Property of 3-Hydroxy-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-hex-5-enoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Hydroxy-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-hex-5-enoic acid tert-butyl ester

There total 6 articles about 3-Hydroxy-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-hex-5-enoic acid tert-butyl 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: 91.0%

3-butenal (7319-38-2) + [(2R,4S,5R)-2-(4-Methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-acetic acid tert-butyl ester (330954-53-5) → 3-Hydroxy-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-hex-5-enoic acid tert-butyl ester (330954-55-7)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; at -78 ℃; for 0.0833333h;

DOI:10.1016/S0040-4020(02)00041-8

Reference yield: 90.0%

5-(2-nitro-phenylselanyl)-pentanal + [(2R,4S,5R)-2-(4-Methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-acetic acid tert-butyl ester (330954-53-5) → 3-Hydroxy-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-hex-5-enoic acid tert-butyl ester (330954-55-7)

Guidance literature:

5-(2-nitro-phenylselanyl)-pentanal; [(2R,4S,5R)-2-(4-Methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-acetic acid tert-butyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran;

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → 3-Hydroxy-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-hex-5-enoic acid tert-butyl ester (330954-55-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran; dimethylformamide / 0.33 h / 20 °C

1.2: 99 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

2.1: 91 percent / n-BuLi; diisopropylamine / tetrahydrofuran; CH₂Cl₂; hexane / 0.08 h / -78 °C

With n-butyllithium; sodium hydride; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)00041-8

upstream raw materials:

[(2R,4S,5R)-2-(4-Methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-acetic acid tert-butyl ester

3-butenal

bromoacetic acid tert-butyl ester

(2R,4R,5R)-5-Hydroxy-2-(4-methoxy-phenyl)-[1,3]dioxane-4-carbaldehyde