Methyl 3-(trimethylsilyl)-4-pentenoate

Base Information

• Chemical Name: Methyl 3-(trimethylsilyl)-4-pentenoate
• CAS No.: 185411-12-5
• Molecular Formula: C9H18O2Si
• Molecular Weight: 186.326
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID70392005
• Nikkaji Number: J2.257.379I
• Mol file: 185411-12-5.mol

Synonyms:185411-12-5;Methyl 3-(trimethylsilyl)-4-pentenoate;Methyl 3-(trimethylsilyl)pent-4-enoate;Methyl 3-trimethylsilylpent-4-enoate;3-(Trimethylsilyl)-4-pentenoic acid methyl ester;4-Pentenoic acid, 3-(trimethylsilyl)-, methyl ester;METHYL3-(TRIMETHYLSILYL)-4-PENTENOATE;SCHEMBL502858;DTXSID70392005;BCP06894;MFCD01863734;AKOS015914428;AM84642;DS-9303;Methyl3-(Trimethylsilyl)Pent-4-Enoate;AC-30882;CS-0022089;FT-0690003;Methyl 3-(trimethylsilyl)-4-pentenoate, 97%;O11894;A880714;A1-01855;J-650386;J-802239

Chemical Property of Methyl 3-(trimethylsilyl)-4-pentenoate

Chemical Property:

• Appearance/Colour: COLORLESS LIQUID
• Vapor Pressure: 1.08mmHg at 25°C
• Refractive Index: n20/D 1.443(lit.)
• Boiling Point: 176.7 °C at 760 mmHg
• Flash Point: 50.9 °C
• PSA: 26.30000
• Density: 0.879 g/cm³
• LogP: 2.44390
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 186.107606347
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

98%, ^*data from raw suppliers

Methyl 3-(trimethylsilyl)-4-pentenoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(C=C)[Si](C)(C)C
• Uses: Methyl 3-(trimethylsilyl)-4-pentenoate, can be used in the synthesis of Eribulin (E615203), a synthetic analog of the marine natural product halichondrin B.

Technology Process of Methyl 3-(trimethylsilyl)-4-pentenoate

There total 1 articles about Methyl 3-(trimethylsilyl)-4-pentenoate 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: 90.0%

Trimethyl orthoacetate (1445-45-0) + (2E)-3-(trimethylsilyl)prop-2-en-1-ol (59376-64-6) → 3-trimethylsilylpent-4-enoic acid methyl ester (185411-12-5)

Guidance literature:

With propionic acid; In toluene; Heating;

DOI:10.1016/S0040-4039(96)01999-5

Reference yield: 99.0%

5-O-benzyl-2,3-O-(3-pentylidene)-β-D-ribofuranosyl fluoride (1002114-93-3) + 3-trimethylsilylpent-4-enoic acid methyl ester (185411-12-5) → methyl 5-[5-O-benzyl-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-3-pentenoate

Guidance literature:

5-O-benzyl-2,3-O-(3-pentylidene)-β-D-ribofuranosyl fluoride; 3-trimethylsilylpent-4-enoic acid methyl ester; In dichloromethane; at 20 ℃; for 0.25h; Molecular sieve;

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.166667h; optical yield given as %de; stereoselective reaction;

DOI:10.1021/ol8018743

Reference yield: 86.0%

2,2-Dimethyl-propionic acid (2R,3S,3aR,5R,6R,7R,7aR)-5,6-diacetoxy-3,7-bis-(tert-butyl-diphenyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-2-ylmethyl ester (870700-46-2) + 3-trimethylsilylpent-4-enoic acid methyl ester (185411-12-5) → (E)-5-[(2R,3S,3aR,5S,6S,7R,7aR)-6-Acetoxy-3,7-bis-(tert-butyl-diphenyl-silanyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-3-enoic acid methyl ester

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 60 ℃; for 16h;

DOI:10.1021/jo051479m

upstream raw materials:

Trimethyl orthoacetate

(2E)-3-(trimethylsilyl)prop-2-en-1-ol

Downstream raw materials:

[(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester

(E)-methyl 5-phenyl-3-(trimethylsilyl)pent-4-enoate

methyl 2-((3aR,4S,5aS,8R,9aS,9bS)-4-((R)-1,2-dihydroxyethyl)octahydrospiro[[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-2,1'-cyclohexan]-8-yl)acetate