132682-21-4

Basic information

• Product Name: Phosphonium, [[(4S)-2-oxo-4-oxazolidinyl]methyl]triphenyl-, iodide
• CAS NO: 132682-21-4
• Molecular Formula: C22H21NO2P.I
• Molecular Weight: 489.293
• Mol File: 132682-21-4.mol

Chemical Properties

• CAS DataBase Reference: Phosphonium, [[(4S)-2-oxo-4-oxazolidinyl]methyl]triphenyl-, iodide(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonium, [[(4S)-2-oxo-4-oxazolidinyl]methyl]triphenyl-, iodide(132682-21-4)
• EPA Substance Registry System: Phosphonium, [[(4S)-2-oxo-4-oxazolidinyl]methyl]triphenyl-, iodide(132682-21-4)

Safety Data

• Hazardous Substances Data: 132682-21-4(Hazardous Substances Data)

Upstream product

• 132682-24-7 (S)-(-)-4-iodomethyl-2-oxazolidinone 
• 603-35-0 triphenylphosphine 

Downstream Products

• 132682-35-0 (Z)-(R)-(+)-3-(2'-phenyl-1'-ethylenyl)-2-oxazolidinone 
• 132682-25-8 (E)-(R)-(+)-3-(2'-phenyl-1'-ethylenyl)-2-oxazolidinone 
• 132682-31-6 (R)-4-[(Z)-2-(3-Methoxy-phenyl)-vinyl]-oxazolidin-2-one 
• 132682-26-9 (R)-4-[(E)-2-(3-Methoxy-phenyl)-vinyl]-oxazolidin-2-one 
• 245106-96-1 (R)-4-((Z)-4-Benzyloxy-but-1-enyl)-oxazolidin-2-one 
• 867154-38-9 (R)-4-[(E)-2-(4-Octyl-phenyl)-vinyl]-oxazolidin-2-one 
• 873222-16-3 (R)-4-(4-octylstyryl)oxazolidine-2-one 

Relevant articles and documents

Design and synthesis of analogues of the sphingosine-1-phosphate receptor 1 agonist IMMH001 with improved phosphorylation rate in human blood

IMMH001, which is a prodrug for sphingosine-1-phosphate receptor 1 (S1P1) agonist, is converted to the active form, its monophosphate ester (S)-IMMH001-P, by sphingosine kinase 1 (SphK1) and sphingosine kinase 2 (SphK2) in vivo. In this study, we designed head-piece-modified analogues of IMMH001 based on structural information and prepared them with an efficient modular synthetic strategy. The analogues showed higher phosphorylation rates in human blood than the parent compound. These results indicated that the pro-R hydroxymethyl in the head-piece-moiety of IMMH001 prevents the pro-S hydroxymethyl from being phosphorylated by the kinase and ATP. The analogues may have better therapeutic potential.

SPHINGOLIPID DERIVATIVES AND THE COMPOSITION FOR ANTI-CANCER CONTAINING THE SAME

Disclosed are a novel sphingolipid derivative having a sphingosine kinase suppressing activity and a composition containing the same. When the newly synthesized sphingolipid derivative of the invention is used, it is possible to maintain concentrations of ceramide and sphingosine to be high by preventing ceramide and sphingosine from being phosphorylated due to sphingosine kinase since an activity of sphingosine kinase is suppressed. In addition, since the apoptosis is induced in a cancer cell by ceramide and sphingosine, it is possible to treat or prevent a cancer or disease related to the cancer. Further, it is possible to treat or prevent a hyper- proliferative disease such as cancer or proliferation-promoting activity of sphingosine kinase. Accordingly, the composition containing the same can be used as a composition for suppressing sphingosine kinase and a composition for treating or preventing a cancer or hyper-proliferative disease.

Synthesis and evaluation of sphingoid analogs as inhibitors of sphingosine kinases

Sphingosine 1-phosphate (S1P), a product of sphingosine kinases (SphK), mediates diverse biological processes such as cell differentiation, proliferation, motility, and apoptosis. In an effort to search and identify specific inhibitors of human SphK, the inhibitory effects of synthetic sphingoid analogs on kinase activity were examined. Among the analogs tested, we found two, SG12 and SG14, that have specific inhibitory effects on hSphK2. N,N-Dimethylsphingosine (DMS), a well-known SphK inhibitor, displayed inhibitory effects for both SphK1 and SphK2, as well as protein kinase C. In contrast, SG12 and SG14 exhibited selective inhibitory effects on hSphK2. Furthermore, SG14 did not affect PKC. In isolated platelets, SG14 blocked the conversion of sphingosine into sphingosine 1-phosphate significantly. This is the first report on the identification of a hSphK2-specific inhibitor, which may provide a useful tool for studying the biological functions of hSphK2.

Investigations of a nucleophilic alaninol synthon derived from serine

A nucleophilic synthon, (S)-(+)-4-(2-oxazolidonyl)-methyltriphenylphosphinyl iodide 6, available from L-serine in five steps (overall yield of 52%), reacts with aldehydes to produce alkenes in good to excellent yields (74-89%) and, in some cases, provides

A NEW NUCLEOPHILIC ALANINOL SYNTHON FROM SERINE

A new nucleophilic alaninol synthon derived from serine is reported.The utility of this reagent in the stereoselective synthesis of β,γ-unsaturated amino alcohols is described.