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

Base Information

• Chemical Name: (4S)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butan-1-ol
• CAS No.: 1431879-69-4
• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.39
• Mol file: 1431879-69-4.mol

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

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

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)butan-1-ol

There total 1 articles about (4S)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butan-1-ol 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: 70.0%

(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)butan-1-ol (1431879-69-4)

Guidance literature:

(R)-4-((S)-1-((4-methoxybenzyl)oxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane; With borane; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol400487e

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:

(4S)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-((4-methoxybenzyl)oxy)butan-1-ol (1431879-69-4) → tert-Butyl(((E)-5-((2R,6R)-6-methoxy-6-((trimethylsilyl)ethynyl)-5,6-dihydro-2Hpyran-2-yl)pent-4-en-1-yl)oxy)diphenylsilane (1431879-77-4)

Guidance literature:

Multi-step reaction with 11 steps

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

1.2: 0.33 h / -60 - 0 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / methanol / 2 h / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.08 h / 0 °C / Inert atmosphere

6.1: chromium dichloride / tetrahydrofuran; 1,4-dioxane / 12 h / 0 - 20 °C / Inert atmosphere

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

7.2: 0.5 h / 20 °C / Inert atmosphere

7.3: 0.08 h / Inert atmosphere

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 0.17 h / 20 °C / pH 7 / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.17 h / 0 °C / Inert atmosphere

10.1: potassium hexamethylsilazane / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

11.1: lithium chloride; tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

With chromium dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 5.1: |Parikh-Doering Oxidation / 6.1: |Takai-Utimoto Olefination;

DOI:10.1021/ol400487e

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

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

(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