(S)-4-((R)-2-(benzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (S)-4-((R)-2-(benzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane
• CAS No.: 135256-43-8
• Molecular Formula: C₁₆H₂₂O₃
• Molecular Weight: 262.349
• Mol file: 135256-43-8.mol

Synonyms:(S)-4-((R)-2-(benzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane

Chemical Property of (S)-4-((R)-2-(benzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-((R)-2-(benzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane

There total 8 articles about (S)-4-((R)-2-(benzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane 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: 92.0%

benzyl bromide (100-39-0) + (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-2-ol (111265-21-5) → (S)-4-((R)-2-(benzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane (135256-43-8)

Guidance literature:

(R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-2-ol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.151027

Reference yield:

((2R,3R)-3-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)oxiran-2-yl)methanol (1191426-29-5) → (S)-4-((R)-2-(benzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane (135256-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

2.1: sodium iodide; zinc / methanol / 8 h / Inert atmosphere; Reflux

3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 6 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; iodine; sodium hydride; triphenylphosphine; sodium iodide; zinc; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tetlet.2019.151027

Reference yield:

methyl (S)-(E)-5,6-di-O-isopropylidene-5,6-dihydroxy-2-hexenoate (123151-78-0) → (S)-4-((R)-2-(benzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane (135256-43-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -15 °C / Inert atmosphere

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate / dichloromethane; decane / 12 h / -20 °C / Inert atmosphere; Molecular sieve

3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

4.1: sodium iodide; zinc / methanol / 8 h / Inert atmosphere; Reflux

5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.2: 6 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; iodine; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; triphenylphosphine; sodium iodide; zinc; In tetrahydrofuran; methanol; decane; dichloromethane; toluene; 2.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1016/j.tetlet.2019.151027

upstream raw materials:

vinyl magnesium bromide

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

benzyl chloride

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

Downstream raw materials:

(R)-2-Benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol

(2S,4R)-2-Benzyloxy-4,5-isopropylidenedioxypentanal

(2S,4R,5RS)-4-O-Benzyl-1,2-O-isopropylidene-5-phthalimido-6-heptene-1,2,4-triol

(2S,4R,5R)-5-Acetamido-4-O-benzyl-1,2-O-isopropylidene-6-heptene-1,2,4-triol