Msdh-C

Base Information

• Chemical Name: Msdh-C
• CAS No.: 144474-37-3
• Molecular Formula: C₂₂H₄₅NO₂S
• Molecular Weight: 387.671
• DSSTox Substance ID: DTXSID30433983
• Wikidata: Q82248272
• Mol file: 144474-37-3.mol

Synonyms:MSDH-C;144474-37-3;N-[(2R,3R)-3-hydroxy-1-methylsulfanylnonan-2-yl]dodecanamide;(2R,3R)-(2-N-Lauroyl)-amino-1-methylthio-3-hydroxynonan;Dodecanamide, N-[(1R,2R)-2-hydroxy-1-[(methylthio)methyl]octyl]-;DTXSID30433983;D-erythro-1-Methylthiohydroceramide;J-007956;N-((2R,3R)-3-Hydroxy-1-(methylthio)nonan-2-yl)dodecanamide

Chemical Property of Msdh-C

Chemical Property:

• PSA: 74.63000
• LogP: 6.47730
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 19
• Exact Mass: 387.31710085
• Heavy Atom Count: 26
• Complexity: 313

Purity/Quality:

95% ^*data from raw suppliers

MSDH-C ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(=O)NC(CSC)C(CCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCC(=O)N[C@@H](CSC)[C@@H](CCCCCC)O
• Uses: MSDH-C is a potent inhibitor of glycosphingolipid biosynthesis.

Technology Process of Msdh-C

There total 3 articles about Msdh-C 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: 83.0%

n-dodecanoyl chloride (112-16-3) + (erythro)-2-Amino-1-methylthio-3-hydroxy-nonane hydrochloride (144474-36-2) → (erythro)-2-(N-Lauroyl)-amino-1-methylthio-3-hydroxy-nonane (144474-37-3)

Guidance literature:

With sodium acetate; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)90177-2

Reference yield:

((R)-1-Methylsulfanylmethyl-2-oxo-octyl)-carbamic acid tert-butyl ester (144474-30-6) → (erythro)-2-(N-Lauroyl)-amino-1-methylthio-3-hydroxy-nonane (144474-37-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / propan-2-ol / 12 h / 0 °C

2: 98 percent / HCl / diethyl ether / 4 h / Ambient temperature

3: 83 percent / NaOAc / tetrahydrofuran

With hydrogenchloride; sodium tetrahydroborate; sodium acetate; In tetrahydrofuran; diethyl ether; isopropyl alcohol;

DOI:10.1016/S0040-4020(01)90177-2

Reference yield:

(erythro)-1-Methylthio-2-(N-tert-butyloxycarbonyl)-amino-3-hydroxynonane (144474-32-8) → (erythro)-2-(N-Lauroyl)-amino-1-methylthio-3-hydroxy-nonane (144474-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / HCl / diethyl ether / 4 h / Ambient temperature

2: 83 percent / NaOAc / tetrahydrofuran

With hydrogenchloride; sodium acetate; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4020(01)90177-2

upstream raw materials:

n-dodecanoyl chloride

(erythro)-2-Amino-1-methylthio-3-hydroxy-nonane hydrochloride

((R)-1-Methylsulfanylmethyl-2-oxo-octyl)-carbamic acid tert-butyl ester

(erythro)-1-Methylthio-2-(N-tert-butyloxycarbonyl)-amino-3-hydroxynonane