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IPTG synthesis

7synthesis methods

Product Name:IPTG
CAS Number:367-93-1
Molecular formula:C9H18O5S
Molecular Weight:238.3

a synthetic method of isopropyl-β-D-thiogalactoside. The steps are as follows:
Step 1: Dissolve β-D-galactose pentaacetate in any organic solvent of methylene chloride, chloroform or 1,2-dichloroethane, and add Lewis acid (boron trifluoride ether, (Aluminum trichloride, zinc chloride) catalyst and potassium ethylxanthate or sodium ethylxanthate are reacted to obtain tetraacetylgalactose ethylxanthate after treatment.
Step 2: Dissolve tetraacetyl galactose ethyl xanthate, 2-bromopropane and sodium carbonate in methanol or ethanol at a temperature of 20°C to 80°C and react for 4-6 hours to obtain isopropyl group after treatment Isopropyl-β-D-thiogalactoside.
synthesis of isopropyl-β-D-thiogalactoside

synthesis of isopropyl-β-D-thiogalactoside

(2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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Yield:367-93-1 98%

Reaction Conditions:

with sodium methylate in methanol at 20; pH=10;

Steps:

1.4

Add 21.4 grams to a 250 ml round bottom flask(52 mmol) isopropyl-β-D thiotetraacetylgalactoside, Then add 50 ml of methanol sodium methoxide solution at pH=10.The reaction is stirred at room temperature for 12 hours to 24 hours.TLC detection,After the reaction is complete, the solvent is removed under reduced pressure.Recrystallization from methanol and acetone gave the desired product 12.1 g.The yield was 98%.

References:

CN103087121,2018,B Location in patent:Paragraph 0013; 0031; 0038-0039