Decanoic acid, 3-hydroxy-, phenylmethyl ester

Base Information

• Chemical Name: Decanoic acid, 3-hydroxy-, phenylmethyl ester
• CAS No.: 132016-02-5
• Molecular Formula: C17H26O3
• Molecular Weight: 278.392
• Mol file: 132016-02-5.mol

Synonyms:

Chemical Property of Decanoic acid, 3-hydroxy-, phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Decanoic acid, 3-hydroxy-, phenylmethyl ester

There total 6 articles about Decanoic acid, 3-hydroxy-, phenylmethyl 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: 89.0%

benzyl 3-oxodecanoate (66696-94-4) → benzyl (±)-3-hydroxydecanoate (132016-02-5)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; water; at 20 ℃; for 1.25h; pH=Ca. 3; Inert atmosphere;

DOI:10.1021/jacs.7b00427

Reference yield: 64.0%

3-hydroxydecanoic acid (5561-87-5,19525-80-5,19526-23-9,33044-91-6,14292-26-3) + benzyl bromide (100-39-0) → benzyl (±)-3-hydroxydecanoate (132016-02-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.bioorg.2019.03.023

Reference yield:

n-octanoic acid chloride (111-64-8) → benzyl (±)-3-hydroxydecanoate (132016-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C / Inert atmosphere

1.3: 3 h / Reflux; Inert atmosphere

2.1: sodium cyanoborohydride; hydrogenchloride / tetrahydrofuran; water / 1.25 h / 20 °C / pH Ca_. 3 / Inert atmosphere

With pyridine; hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; water;

DOI:10.1021/jacs.7b00427

upstream raw materials:

benzyl 3-oxodecanoate

n-octanoic acid chloride

benzyl alcohol

3-hydroxydecanoic acid

Downstream raw materials:

phenylmethyl (3R)-3-[(2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl)oxy]decanoate

phenylmethyl (3R)-3-[(2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl)oxy]decanoate

(R)-3-(((R)-3-[α-L-rhamnopyranosyl]decanoyl)oxy)decanoic acid

(S)-3-(((R)-3-[α-L-rhamnopyranosyl]decanoyl)oxy)decanoic acid

Refernces

• 1、 Jovanovic, Milos,Radivojevic, Jelena,O'Connor, Kevin,Blagojevic, Stevan,Begovic, Biljana,Lukic, Vera,Nikodinovic-Runic, Jasmina,Savic, Vladimir. "Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans". supporting information. p. 209 - 217. Retrieved 2019/03/23.