SPICULISPORIC ACID

Base Information

• Chemical Name: SPICULISPORIC ACID
• CAS No.: 469-77-2
• Molecular Formula: C₁₇H₂₈O₆
• Molecular Weight: 328.406
• Hs Code.: 2932190090
• Mol file: 469-77-2.mol

Synonyms:2-Furanaceticacid, 2-carboxy-a-decyltetrahydro-5-oxo-(8CI); 2-Furanacetic acid, 2-carboxy-a-decyltetrahydro-5-oxo-, [S-(R*,R*)]-;(-)-Spiculisporic acid; NSC 244387; Spiculisporic acid

Chemical Property of SPICULISPORIC ACID

Chemical Property:

• Melting Point: 145 °C
• Boiling Point: 549°Cat760mmHg
• PKA: 2.13±0.20(Predicted)
• Flash Point: 195.4°C
• PSA: 100.90000
• Density: 1.163g/cm³
• LogP: 3.37840
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,5-Dicarboxy-γ-pentadecanolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of SPICULISPORIC ACID

There total 7 articles about SPICULISPORIC ACID 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: 76.0%

(2S,1'S)-2-(1'-tert-butoxycarbonyl-undecyl)-5-oxo-tetrahydrofuran-2-carboxylic acid methyl ester (500785-91-1) → spiculisporic acid (469-77-2)

Guidance literature:

(2S,1'S)-2-(1'-tert-butoxycarbonyl-undecyl)-5-oxo-tetrahydrofuran-2-carboxylic acid methyl ester; With sodium hydroxide; In tetrahydrofuran; at 100 ℃; for 5.5h;

With hydrogenchloride; In tetrahydrofuran; at 100 ℃; for 3.5h; Further stages.;

DOI:10.1021/ja029095q

Reference yield:

(2S,1'S)-2-(1'-tert-butoxycarbonyl-undec-3'-enyl)-5-oxo-2,5-dihydrofuran-2-carboxylic acid methyl ester (500785-90-0) → spiculisporic acid (469-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

2.1: aq.NaOH / tetrahydrofuran / 5.5 h / 100 °C

2.2: 76 percent / aq. HCl / tetrahydrofuran / 3.5 h / 100 °C

With sodium hydroxide; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/ja029095q

Reference yield:

1,1-diiodooctane (66225-22-7) → spiculisporic acid (469-77-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 65 percent / CrCl₂:DMF complex / tetrahydrofuran / 3.5 h

2.1: 92 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

3.1: aq.NaOH / tetrahydrofuran / 5.5 h / 100 °C

3.2: 76 percent / aq. HCl / tetrahydrofuran / 3.5 h / 100 °C

With sodium hydroxide; CrCl₂*DMF; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/ja029095q

upstream raw materials:

trimethyl (2S,3S)-decylcitrate

(2S,1'S)-2-(1'-tert-butoxycarbonyl-undecyl)-5-oxo-tetrahydrofuran-2-carboxylic acid methyl ester

(2S,1'S)-2-(1'-tert-butoxycarbonyl-undec-3'-enyl)-5-oxo-2,5-dihydrofuran-2-carboxylic acid methyl ester

1,1-diiodooctane

Refernces

• 1、 Brandaenge, Svante,Dahlman, Olof,Lindqvist, Bo,Mahlen, Anders,Moerch, Lars. "Absolute Configuration and Enantioselective Synthesis of Spiculisporic Acid". . p. 837 - 844. Retrieved 2007/10/02.