IM 2 autoregulator

Base Information

• Chemical Name: IM 2 autoregulator
• CAS No.: 124753-55-5
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.224
• Mol file: 124753-55-5.mol

Synonyms:2(3H)-Furanone,dihydro-3-(1-hydroxybutyl)-4-(hydroxymethyl)-, [3R-[3a(R*),4b]]-; IM 2; IM 2 (autoregulator)

Chemical Property of IM 2 autoregulator

Chemical Property:

• Vapor Pressure: 5.09E-05mmHg at 25°C
• Boiling Point: 311.2°C at 760 mmHg
• Flash Point: 134.5°C
• PSA: 46.53000
• Density: 1.06g/cm³
• LogP: 0.95650

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of IM 2 autoregulator

There total 8 articles about IM 2 autoregulator 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%

(3R,4S)-4-(((tert-butyldimethylsilyl)oxy)methyl)-3-((R)-1-hydroxybutyl)dihydrofuran-2(3H)-one → (3R,4R)-3-((R)-1-hydroxybutyl)-4-(hydroxymethyl)dihydrofuran-2(3H)-one (124753-55-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 12h;

DOI:10.1021/acs.joc.8b00122

Reference yield:

C9H14O5 → (3R,4R)-3-((R)-1-hydroxybutyl)-4-(hydroxymethyl)dihydrofuran-2(3H)-one (124753-55-5)

Guidance literature:

C₉H₁₄O₅; With dimethyl sulfide borane; In tetrahydrofuran; at 0 ℃; for 3h;

With methanol; In tetrahydrofuran; at 30 ℃;

DOI:10.1039/b812698d

Reference yield:

(-)-(S)-5-oxotetrahydro-3-furancarboxylic acid (4694-66-0) → (3R,4R)-3-((R)-1-hydroxybutyl)-4-(hydroxymethyl)dihydrofuran-2(3H)-one (124753-55-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 0 °C

2.1: 1H-imidazole / dichloromethane / 24 h / 20 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

4.1: hydrogenchloride / tetrahydrofuran; diethyl ether / 12 h / 0 - 20 °C

With 1H-imidazole; hydrogenchloride; dimethylsulfide borane complex; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/acs.joc.8b00122

upstream raw materials:

(-)-(S)-5-oxotetrahydro-3-furancarboxylic acid

(R)-4-(hydroxymethyl)dihydrofuran-2(3H)-one

Refernces

• 1、 Elsner, Petteri,Jiang, Hao,Nielsen, Johanne B.,Pasi, Filippo,Jorgensen, Karl Anker. "A modular and organocatalytic approach to γ-butyrolactone autoregulators from Streptomycetes". . p. 5827 - 5829. Retrieved 2008.