(R)-Methyl 3-(benzyloxy)butanoate

Base Information

• Chemical Name: (R)-Methyl 3-(benzyloxy)butanoate
• CAS No.: 116761-24-1
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.257
• DSSTox Substance ID: DTXSID60465777
• Wikidata: Q82291993
• Mol file: 116761-24-1.mol

Synonyms:(R)-Methyl 3-(benzyloxy)butanoate;116761-24-1;(R)-Methyl3-(benzyloxy)butanoate;methyl (3R)-3-phenylmethoxybutanoate;DTXSID60465777;methyl (R)-3-(benzyloxy)butanoate

Chemical Property of (R)-Methyl 3-(benzyloxy)butanoate

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 185

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CC(=O)OC)OCC1=CC=CC=C1
• Isomeric SMILES: C[C@H](CC(=O)OC)OCC1=CC=CC=C1

Technology Process of (R)-Methyl 3-(benzyloxy)butanoate

There total 3 articles about (R)-Methyl 3-(benzyloxy)butanoate 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: 94.0%

Methyl (R)-3-hydroxybutyrate (3976-69-0) + benzyl bromide (100-39-0) → (R)-3-(benzyloxy)butanoic acid methyl ester (116761-24-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201410371

Reference yield: 86.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + Methyl (R)-3-hydroxybutyrate (3976-69-0) → (R)-3-(benzyloxy)butanoic acid methyl ester (116761-24-1)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; Ambient temperature;

DOI:10.1002/hlca.19880710119

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (R)-3-(benzyloxy)-butanoic acid (116838-41-6) → (R)-3-(benzyloxy)butanoic acid methyl ester (116761-24-1)

Guidance literature:

In diethyl ether; Product distribution;

DOI:10.1002/(SICI)1522-2675(19981216)81:12<2430::AID-HLCA2430>3.0.CO;2-W

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

Methyl (R)-3-hydroxybutyrate

diazomethane

(R)-3-(benzyloxy)-butanoic acid

Downstream raw materials:

(R)-3-(benzyloxy)-butanoic acid

(3R)-3-(<(3'R)-3'-(benzyloxy)butanoyl>oxy)butanoate

(2S,3S,5R)-5-Benzyloxy-1-[(4-methoxy-phenyl)-diphenyl-methoxy]-3-methyl-hexan-2-ol

(2S,3S,5R)-2,5-Bis-benzyloxy-3-methyl-hexanal

Refernces

• 1、 -. "MULTIBIOTIC AGENTS AND METHODS OF USING THE SAME". Page/Page column 109. . Retrieved 2019/01/06.
• 2、 Anderson, Katie,Laclef, Sylvain,Barrett, Anthony G.M.. "Mechanistic studies of highly regioselective decarboxylative-prenyl migration reactions of prenyloxycarbonyl-diketo-dioxinones". . p. 5569 - 5579. Retrieved 2015/03/30.