(3R,4R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3-methylbutyraldehyde

Base Information

• Chemical Name: (3R,4R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3-methylbutyraldehyde
• CAS No.: 921763-73-7
• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.455
• Mol file: 921763-73-7.mol

Synonyms:(3R,4R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3-methylbutyraldehyde

Chemical Property of (3R,4R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3-methylbutyraldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3-methylbutyraldehyde

There total 3 articles about (3R,4R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3-methylbutyraldehyde 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:

(S)-2,2-diethyl-4-[(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-but-3-enyl]-[1,3]dioxolane (921763-72-6) → (3R,4R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3-methylbutyraldehyde (921763-73-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 9-BBN / tetrahydrofuran / 3 h / Heating

1.2: 94 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 17 h / 20 °C

2.1: 89 percent / SO₃*pyridine; DMSO; i-Pr₂NEt / CH₂Cl₂ / 0.5 h / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2007.02.058

Reference yield:

(1R,2R)-1-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-methyl-but-3-en-1-ol (179943-76-1) → (3R,4R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3-methylbutyraldehyde (921763-73-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 16 h / Heating

2.1: 9-BBN / tetrahydrofuran / 3 h / Heating

2.2: 94 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 17 h / 20 °C

3.1: 89 percent / SO₃*pyridine; DMSO; i-Pr₂NEt / CH₂Cl₂ / 0.5 h / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2007.02.058

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (3R,4R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3-methylbutyraldehyde (921763-73-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 16 h / Heating

2.1: 9-BBN / tetrahydrofuran / 3 h / Heating

2.2: 94 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 17 h / 20 °C

3.1: 89 percent / SO₃*pyridine; DMSO; i-Pr₂NEt / CH₂Cl₂ / 0.5 h / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2007.02.058

upstream raw materials:

(S)-2,2-diethyl-4-[(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-but-3-enyl]-[1,3]dioxolane

p-methoxybenzyl chloride

(1R,2R)-1-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-methyl-but-3-en-1-ol

Downstream raw materials:

(2R,3R)-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynal

(2S,3R,4R)-3-(4-methoxy-benzyloxy)-4-methyl-hept-6-yne-1,2-diol

(S)-2,2-diethyl-4-[(1R,2R)-1-(4-methoxybenzyloxy)-2-methylpent-4-ynyl]-[1,3]dioxolane

1-[(1R,2S,3R)-3-(dimethyl-phenyl-silanyl)-1-((R)-1-methyl-but-3-ynyl)-2-triethylsilanyloxypent-4-enyloxymethyl]-4-methoxy-benzene