(2R,3R)-3-hydroxy-3-isopropyl-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-4-pentynoic acid

Base Information

• Chemical Name: (2R,3R)-3-hydroxy-3-isopropyl-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-4-pentynoic acid
• CAS No.: 647029-38-7
• Molecular Formula: C₂₃H₂₄O₆
• Molecular Weight: 396.44
• Mol file: 647029-38-7.mol

Synonyms:(2R,3R)-3-hydroxy-3-isopropyl-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-4-pentynoic acid

Chemical Property of (2R,3R)-3-hydroxy-3-isopropyl-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-4-pentynoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-hydroxy-3-isopropyl-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-4-pentynoic acid

There total 5 articles about (2R,3R)-3-hydroxy-3-isopropyl-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-4-pentynoic 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:

(2R,3R)-2-Benzo[1,3]dioxol-5-ylmethyl-3-hydroxy-3-isopropyl-5-(4-methoxy-phenyl)-pent-4-ynal (647029-44-5) → (2R,3R)-3-hydroxy-3-isopropyl-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-4-pentynoic acid (647029-38-7)

Guidance literature:

With sodium chlorite; sodium dihydrogen phosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 0 ℃; for 1h;

DOI:10.1271/bbb.67.2183

Reference yield:

(2S)-1-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)methyl-4-pentyn-3-one (647029-35-4) → (2R,3R)-3-hydroxy-3-isopropyl-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-4-pentynoic acid (647029-38-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium / tetrahydrofuran

1.2: 66.6 percent / tetrahydrofuran / 1 h / -78 °C

2.1: N-methylmorpholine N-oxide; molecular sieves 4 Angstroem; tetrapropylammonium perruthenate / CH₂Cl₂ / 6 h / 20 °C

3.1: sodium dihydrogen phosphate; 2-methyl-2-butene; sodium chlorite / H₂O; 2-methyl-propan-2-ol / 1 h / 0 °C

With sodium chlorite; tetrapropylammonium perruthennate; sodium dihydrogen phosphate; 2-methyl-but-2-ene; 4 A molecular sieve; magnesium; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1.2: Grignard reaction;

DOI:10.1271/bbb.67.2183

Reference yield:

(2S)-1-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)methyl-4-pentyn-3-one (647029-33-2) → (2R,3R)-3-hydroxy-3-isopropyl-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-4-pentynoic acid (647029-38-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86.6 percent / acetic acid / tetrahydrofuran; H₂O / 15 h / 20 °C

2.1: magnesium / tetrahydrofuran

2.2: 66.6 percent / tetrahydrofuran / 1 h / -78 °C

3.1: N-methylmorpholine N-oxide; molecular sieves 4 Angstroem; tetrapropylammonium perruthenate / CH₂Cl₂ / 6 h / 20 °C

4.1: sodium dihydrogen phosphate; 2-methyl-2-butene; sodium chlorite / H₂O; 2-methyl-propan-2-ol / 1 h / 0 °C

With sodium chlorite; tetrapropylammonium perruthennate; sodium dihydrogen phosphate; 2-methyl-but-2-ene; 4 A molecular sieve; magnesium; acetic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 2.2: Grignard reaction;

DOI:10.1271/bbb.67.2183

upstream raw materials:

(2R,3R)-2-Benzo[1,3]dioxol-5-ylmethyl-3-hydroxy-3-isopropyl-5-(4-methoxy-phenyl)-pent-4-ynal

(2S)-1-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)methyl-4-pentyn-3-one

(2S,3R)-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentyne-1,3-diol

(2S)-1-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)methyl-4-pentyn-3-one