(4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal

Base Information

• Chemical Name: (4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal
• CAS No.: 1431879-70-7
• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.375
• Mol file: 1431879-70-7.mol

Synonyms:(4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal

Chemical Property of (4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal

There total 2 articles about (4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal 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: 99.0%

(4S)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butan-1-ol (1431879-69-4) → (4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal (1431879-70-7)

Guidance literature:

(4S)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butan-1-ol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 - -60 ℃; for 1h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -60 - 0 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1021/ol400487e

Reference yield:

(R)-4-((S)-1-((4-methoxybenzyl)oxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane → (4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal (1431879-70-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: borane / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 - -60 °C / Inert atmosphere

2.2: 0.33 h / -60 - 0 °C / Inert atmosphere

With oxalyl dichloride; borane; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;

DOI:10.1021/ol400487e

Reference yield: 87.0%

(4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal (1431879-70-7) + trimethylsilylacetylene (1066-54-2) → (6S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)-1-(trimethylsilyl)hex-1-yn-3-ol (1431879-85-4)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

(4S)-4-((4R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butanal; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol400487e

upstream raw materials:

(4S)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butan-1-ol

Downstream raw materials:

tert-Butyl(((E)-5-((2R,6R)-6-methoxy-6-((trimethylsilyl)ethynyl)-5,6-dihydro-2Hpyran-2-yl)pent-4-en-1-yl)oxy)diphenylsilane

tert-butyl(((E)-5-((2R,6R)-6-(iodoethynyl)-6-methoxy-5,6-dihydro-2H-pyran-2-yl)pent-4-en-1-yl)oxy)diphenylsilane

(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate

(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2S,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopentyl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethyl pivalate