144474-37-3

Basic information

• Product Name: (2R,3R)-(2-N-LAUROYL)-AMINO-1-METHYLTHIO-3-HYDROXYNONAN
• Synonyms: D-ERYTHRO-1-METHYLTHIOHYDROCERAMIDE;(2R,3R)-(2-N-LAUROYL)-AMINO-1-METHYLTHIO-3-HYDROXYNONAN;MSDH-C
• CAS NO: 144474-37-3
• Molecular Formula: C22H45NO2S
• Molecular Weight: 387.66
• Mol File: 144474-37-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R,3R)-(2-N-LAUROYL)-AMINO-1-METHYLTHIO-3-HYDROXYNONAN(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-(2-N-LAUROYL)-AMINO-1-METHYLTHIO-3-HYDROXYNONAN(144474-37-3)
• EPA Substance Registry System: (2R,3R)-(2-N-LAUROYL)-AMINO-1-METHYLTHIO-3-HYDROXYNONAN(144474-37-3)

Safety Data

• Hazardous Substances Data: 144474-37-3(Hazardous Substances Data)

Usage

Uses

MSDH-C is a potent inhibitor of glycosphingolipid biosynthesis.

Upstream product

• 112-16-3 n-dodecanoyl chloride 
• 144474-36-2 (erythro)-2-Amino-1-methylthio-3-hydroxy-nonane hydrochloride 
• 144474-32-8 (erythro)-1-Methylthio-2-(N-tert-butyloxycarbonyl)-amino-3-hydroxynonane 
• 144474-30-6 ((R)-1-Methylsulfanylmethyl-2-oxo-octyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Synthesis of potential inhibitors of the glycosphingolipid biosynthesis

A synthesis of ceramide analogs 6 and 7 is reported here starting from L-cysteine. Alkylation of 2 and subsequent reduction of the intermediate formed ketone 3 afforded the diastereomeric alcohols 4. Deprotection and acylation of 4 lead to the desired product 6 which is converted to the sulfonium salt 7. Compound 6 is a powerful inhibitor of the glycosphingolipid biosynthesis.