Sitophilate

Base Information

• Chemical Name: Sitophilate
• CAS No.: 114607-20-4
• Molecular Formula: C11H22 O3
• Molecular Weight: 202.29
• DSSTox Substance ID: DTXSID00150796
• Nikkaji Number: J785.511G
• Wikidata: Q83016999
• Mol file: 114607-20-4.mol

Synonyms:sitophilate

Chemical Property of Sitophilate

Chemical Property:

• Vapor Pressure: 0.000368mmHg at 25°C
• Boiling Point: 283.4°Cat760mmHg
• PKA: 14.45±0.20(Predicted)
• Flash Point: 108.6°C
• PSA: 46.53000
• Density: 0.953g/cm³
• LogP: 2.12520
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 202.15689456
• Heavy Atom Count: 14
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)OC(=O)C(C)C(CC)O
• Isomeric SMILES: CC[C@H]([C@H](C)C(=O)OC(CC)CC)O

Technology Process of Sitophilate

There total 27 articles about Sitophilate 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: 80.0%

1-ethylpropyl (2SR,3RS)-3-tert-butyldimethylsilyloxy-2-methylpentanoate → 1-ethylpropyl (2SR,3RS)-3-hydroxy-2-methylpentanoate (114607-20-4,114715-56-9,122798-52-1,122798-53-2,122798-54-3,124753-52-2,129314-00-7,129314-02-9)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(01)00647-0

Reference yield: 79.0%

(2SR,3RS)-3-hydroxy-2-methylpentanoic acid (28892-73-1,77302-11-5,77405-43-7,81873-63-4,93861-71-3,98524-11-9,98524-12-0,109215-41-0,131897-89-7) + 2-pentanol (584-02-1) → 1-ethylpropyl (2SR,3RS)-3-hydroxy-2-methylpentanoate (114607-20-4,114715-56-9,122798-52-1,122798-53-2,122798-54-3,124753-52-2,129314-00-7,129314-02-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; 1.) -10 deg C, 30 min, 2.) 25 deg C, 2 h;

Reference yield: 78.0%

2-Methylene-3-hydroxypentanoic acid 3-pentyl ester (129277-93-6) → 2-Methyl-3-hydroxypentanoic acid threo-3-pentyl ester (114607-20-4,114715-56-9,122798-52-1,122798-53-2,122798-54-3,124753-52-2,129314-00-7,129314-02-9) + 1-ethylpropyl (2SR,3RS)-3-hydroxy-2-methylpentanoate (114607-20-4,114715-56-9,122798-52-1,122798-53-2,122798-54-3,124753-52-2,129314-00-7,129314-02-9)

Guidance literature:

With hydrogen; nickel; In ethanol; at 25 ℃; for 0.166667h; under 760 Torr; Product distribution; other reducing agents, other solvents, other reaction times; stereoselectivity;

DOI:10.1007/BF00960333

upstream raw materials:

2-Methylene-3-hydroxypentanoic acid 3-pentyl ester

sec-Amyl propionate

propionaldehyde

3-pentanol ester of 2-bromopropionic acid

Downstream raw materials:

(2S,3R)-2-Methyl-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-pentanoic acid 1-ethyl-propyl ester

Refernces

Optically Active Organoiron Complexes in Synthesis. An Enantioface Selective 3-Hydroxypropionate-2,3-Dication Equivalent

10.1016/S0040-4039(00)91888-4

The research focuses on the application of optically active organoiron complexes as chiral 3-hydroxypropionate-2,3-dication equivalents in asymmetric synthesis. The purpose of the study was to demonstrate the enantioface-selective synthesis of 2,3-disubstituted 3-hydroxypropionates using a series of transformations involving the addition of nucleophiles to organoiron complexes, followed by redox-promoted carboxylation. The key chemicals used in the process include Fp(q^2-1,2-dimethoxyethylene)BF, (R,R)-butane-2,3-dial, lithium dimethylcuprate, p-methoxybenzyl alcohol, ethyl Grignard, and various reagents for oxidation and deprotection steps. The conclusions drawn from the research indicate that the organoiron complexes can serve as effective enantioface-selective equivalents, leading to the synthesis of optically active compounds such as (2R,3S)-methyl-2-methyl-3-p-methoxybenzyloxypentanoate and enantio-pure sitophilate, the latter being the enantiomer of the granary weevil aggregation pheromone. The study also suggests potential for further exploration in the preparation of syn- or anti-diastereomers of β-hydroxyesters using this methodology.