(4R,5S)-4-(tert-butyldiphenylsilyloxy)methyl-5-(3,4-methylenedioxyphenyl)dihydro-3(2H)-furanone

Base Information

• Chemical Name: (4R,5S)-4-(tert-butyldiphenylsilyloxy)methyl-5-(3,4-methylenedioxyphenyl)dihydro-3(2H)-furanone
• CAS No.: 189557-90-2
• Molecular Formula: C₂₈H₃₀O₅Si
• Molecular Weight: 474.629
• Mol file: 189557-90-2.mol

Synonyms:(4R,5S)-4-(tert-butyldiphenylsilyloxy)methyl-5-(3,4-methylenedioxyphenyl)dihydro-3(2H)-furanone

Chemical Property of (4R,5S)-4-(tert-butyldiphenylsilyloxy)methyl-5-(3,4-methylenedioxyphenyl)dihydro-3(2H)-furanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-4-(tert-butyldiphenylsilyloxy)methyl-5-(3,4-methylenedioxyphenyl)dihydro-3(2H)-furanone

There total 24 articles about (4R,5S)-4-(tert-butyldiphenylsilyloxy)methyl-5-(3,4-methylenedioxyphenyl)dihydro-3(2H)-furanone 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: 87.0%

(2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran (302605-77-2) → (4R,5S)-4-(tert-butyldiphenylsilyloxy)methyl-5-(3,4-methylenedioxyphenyl)dihydro-3(2H)-furanone (189557-90-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -75 ℃; for 1h;

DOI:10.1271/bbb.64.1563

Reference yield:

piperonal (120-57-0,30024-74-9) → (4R,5S)-4-(tert-butyldiphenylsilyloxy)methyl-5-(3,4-methylenedioxyphenyl)dihydro-3(2H)-furanone (189557-90-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: diisopropylamine; n-BuLi / tetrahydrofuran / 0.5 h / -75 °C

1.2: 46 percent / tetrahydrofuran / 0.5 h / -75 °C

2.1: 82 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

3.1: LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

4.1: 80 percent / pyridine / 0.5 h / 20 °C

5.1: 77 percent / formic acid / diethyl ether / 0.5 h / 20 °C

6.1: 85 percent / NaIO₄ / methanol / 2 h / 20 °C

7.1: pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 0.5 h / Heating

7.2: 77 percent / NaBH₄ / ethanol / 0.5 h / 20 °C

8.1: 61 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 20 °C

9.1: 55 percent / diisobutylaluminium hydride / CH₂Cl₂; toluene / 0.5 h / -75 °C

10.1: 88 percent / HCl / ethanol / 0.5 h / Heating

11.1: 86 percent / imidazole / dimethylformamide / 1 h / 20 °C

12.1: 87 percent / dimethyl sulfoxide; oxalyl chloride / CH₂Cl₂ / 1 h / -75 °C

With 1H-imidazole; hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Metallation / 1.2: Addition / 2.1: Etherification / 3.1: Reduction / 4.1: Acylation / 5.1: Detritylation / 6.1: Oxidation / 7.1: Reduction / 7.2: Reduction / 8.1: Dehydration / 9.1: Reduction / 10.1: Hydrolysis / 11.1: Silylation / 12.1: Swern oxidation;

DOI:10.1271/bbb.64.1563

Reference yield:

(2S,3S,4S)-4-hydroxy-3-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran (302605-76-1) → (4R,5S)-4-(tert-butyldiphenylsilyloxy)methyl-5-(3,4-methylenedioxyphenyl)dihydro-3(2H)-furanone (189557-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / imidazole / dimethylformamide / 1 h / 20 °C

2: 87 percent / dimethyl sulfoxide; oxalyl chloride / CH₂Cl₂ / 1 h / -75 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; N,N-dimethyl-formamide; 1: Silylation / 2: Swern oxidation;

DOI:10.1271/bbb.64.1563

upstream raw materials:

(3R,4S,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

(2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

piperonal

(2S,3S,4S)-4-hydroxy-3-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

Downstream raw materials:

((2S,3R)-2-Benzo[1,3]dioxol-5-yl-4-methylene-tetrahydro-furan-3-ylmethoxy)-tert-butyl-diphenyl-silane

(2S,3R,4R)-4-benzyl-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

(3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-3-carbaldehyde

(3S,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-((R)-benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol