(E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one

Base Information

• Chemical Name: (E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one
• CAS No.: 287119-18-0
• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.359
• Mol file: 287119-18-0.mol

Synonyms:(E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one

Chemical Property of (E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one

There total 5 articles about (E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one 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:

benzyl bromide (100-39-0) → (E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one (287119-18-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / Bu₄NI; Ag₂O / CH₂Cl₂

2: 100 percent / LiAlH₄ / tetrahydrofuran / Heating

3: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 °C

4: tetrahydrofuran / 8 h / Heating

With lithium aluminium tetrahydride; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; silver(l) oxide; In tetrahydrofuran; dichloromethane; 1: Etherification / 2: Reduction / 3: Oxidation / 4: Condensation;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<943::AID-HLCA943>3.0.CO;2-H

Reference yield:

ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate (114184-94-0) → (E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one (287119-18-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / Bu₄NI; Ag₂O / CH₂Cl₂

2: 100 percent / LiAlH₄ / tetrahydrofuran / Heating

3: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 °C

4: tetrahydrofuran / 8 h / Heating

With lithium aluminium tetrahydride; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; silver(l) oxide; In tetrahydrofuran; dichloromethane; 1: Etherification / 2: Reduction / 3: Oxidation / 4: Condensation;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<943::AID-HLCA943>3.0.CO;2-H

Reference yield:

1-O-benzyl-3,4-O-isopropylidene-D-erythritol (12) and 2-O-benzyl-3,4-O-isopropylidene-D-erythritol (111462-38-5) → (E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one (287119-18-0)

Guidance literature:

Multi-step reaction with 2 steps

1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 °C

2: tetrahydrofuran / 8 h / Heating

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Oxidation / 2: Condensation;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<943::AID-HLCA943>3.0.CO;2-H

upstream raw materials:

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

1-triphenylphosphoranylidene-2-propanone

ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate

benzyl bromide

Downstream raw materials:

[(E)-(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methylene-but-2-enyloxy]-tert-butyl-dimethyl-silane