4-Pentenoic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Base Information

• Chemical Name: 4-Pentenoic acid, 2-(triphenylphosphoranylidene)-, methyl ester
• CAS No.: 95561-65-2
• Molecular Formula: C24H23O2P
• Molecular Weight: 374.419
• DSSTox Substance ID: DTXSID50453643
• Wikidata: Q82274839

Synonyms:4-Pentenoic acid, 2-(triphenylphosphoranylidene)-, methyl ester;95561-65-2;SCHEMBL13719255;DTXSID50453643

Chemical Property of 4-Pentenoic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Chemical Property:

• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 374.14356697
• Heavy Atom Count: 27
• Complexity: 494

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)CC=C

Technology Process of 4-Pentenoic acid, 2-(triphenylphosphoranylidene)-, methyl ester

There total 2 articles about 4-Pentenoic acid, 2-(triphenylphosphoranylidene)-, methyl ester 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: 86.0%

but-3-en-1-yltriphenylphosphonium bromide (16958-42-2) + methyl chloroformate (79-22-1) → Triphenylphosphin-allyl-methoxycarbonyl-methylen (95561-65-2)

Guidance literature:

but-3-en-1-yltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 - 0 ℃; for 0.5h;

methyl chloroformate; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 1h;

DOI:10.1002/ejoc.201601197

Reference yield:

triphenylphosphine (603-35-0) → Triphenylphosphin-allyl-methoxycarbonyl-methylen (95561-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene / 24 h / Inert atmosphere; Reflux

2.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 1.5 h / -78 - 20 °C / Inert atmosphere

With potassium hexamethylsilazane; In tetrahydrofuran; toluene;

DOI:10.1039/c3ob42191k

Reference yield: 73.0%

(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxolane-4-carbaldehyde + Triphenylphosphin-allyl-methoxycarbonyl-methylen (95561-65-2) → 2-[1-[(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-pent-4-enoic acid methyl ester

Guidance literature:

In toluene; for 17h; Ambient temperature;

DOI:10.1055/s-1999-2744

upstream raw materials:

but-3-en-1-yltriphenylphosphonium bromide

methyl chloroformate

triphenylphosphine

Downstream raw materials:

(E)-(4S,5R)-2-Allyl-4,5-dihydroxy-5-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-pent-2-enoic acid methyl ester

(E)-(4S,5S)-2-Allyl-5-(4-methoxy-benzyloxymethoxy)-5-((2R,4S,5R)-2-phenyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl)-4-triethylsilanyloxy-pent-2-en-1-ol

(E)-(4S,5S)-2-Allyl-5-(4-methoxy-benzyloxymethoxy)-5-((2R,4S,5R)-2-phenyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl)-4-triethylsilanyloxy-pent-2-enoic acid methyl ester

(2R,4S,5R)-4-[(E)-(1S,2S)-1-(4-Methoxy-benzyloxymethoxy)-4-methoxymethoxymethyl-2-triethylsilanyloxy-hepta-3,6-dienyl]-2-phenyl-5-triethylsilanyloxy-[1,3]dioxane

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