1-Pentyn-3-one, 5-(1,3-benzodioxol-5-yl)-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]- 1-(4-methoxyphenyl)-, (4S)-

Base Information

• Chemical Name: 1-Pentyn-3-one, 5-(1,3-benzodioxol-5-yl)-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]- 1-(4-methoxyphenyl)-, (4S)-
• CAS No.: 647029-33-2
• Molecular Formula: C26H32O5Si
• Molecular Weight: 452.623
• Mol file: 647029-33-2.mol

Synonyms:

Chemical Property of 1-Pentyn-3-one, 5-(1,3-benzodioxol-5-yl)-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]- 1-(4-methoxyphenyl)-, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Pentyn-3-one, 5-(1,3-benzodioxol-5-yl)-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]- 1-(4-methoxyphenyl)-, (4S)-

There total 1 articles about 1-Pentyn-3-one, 5-(1,3-benzodioxol-5-yl)-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]- 1-(4-methoxyphenyl)-, (4S)- 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: 84.1%

1-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)methyl-4-pentyn-3-ol → (2S)-1-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)methyl-4-pentyn-3-one (647029-33-2)

Guidance literature:

With pyridinium trifluroacetate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In toluene; at 20 ℃; for 24h;

DOI:10.1271/bbb.67.2183

Reference yield: 86.6%

(2S)-1-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)methyl-4-pentyn-3-one (647029-33-2) → (2S)-1-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)methyl-4-pentyn-3-one (647029-35-4)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 20 ℃; for 15h;

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)-2-Benzo[1,3]dioxol-5-ylmethyl-3-hydroxy-3-isopropyl-5-(4-methoxy-phenyl)-pent-4-ynal (647029-44-5)

Guidance literature:

Multi-step reaction with 3 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

With tetrapropylammonium perruthennate; 4 A molecular sieve; magnesium; acetic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; 2.2: Grignard reaction;

DOI:10.1271/bbb.67.2183

Downstream raw materials:

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

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

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

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