114299-64-8

Basic information

• Product Name: (2S,3R,4E)-2-AZIDO-3-(TERT-BUTYLDIMETHYLSILYL)-ERYTHRO-SPHINGOSINE
• Synonyms: (2S,3R,4E)-2-AZIDO-3-(TERTBUTYLDIMETHYLSILYL)-4-OCTADECENE-3-OL;(2S,3R,4E)-2-AZIDO-3-(TERT-BUTYLDIMETHYLSILYL)-ERYTHRO-SPHINGOSINE
• CAS NO: 114299-64-8
• Molecular Formula: C₂₄H₄₉N₃O₂Si
• Molecular Weight: 439.75
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators
• Mol File: 114299-64-8.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (2S,3R,4E)-2-AZIDO-3-(TERT-BUTYLDIMETHYLSILYL)-ERYTHRO-SPHINGOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-2-AZIDO-3-(TERT-BUTYLDIMETHYLSILYL)-ERYTHRO-SPHINGOSINE(114299-64-8)
• EPA Substance Registry System: (2S,3R,4E)-2-AZIDO-3-(TERT-BUTYLDIMETHYLSILYL)-ERYTHRO-SPHINGOSINE(114299-64-8)

Safety Data

• Hazardous Substances Data: 114299-64-8(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

InChI:InChI=1/C24H49N3O2Si/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(22(21-28)26-27-25)29-30(5,6)24(2,3)4/h19-20,22-23,28H,7-18,21H2,1-6H3/b20-19+/t22-,23+/m0/s1

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 117606-36-7 (4S)-3-<(2'R,3'R,4'E)-2'-azido-3'-hydroxy-4'-octadecenoyl>-4-(isopropyl)-2-oxazolidinone 
• 117606-37-8 (4S)-3-<(2'R,3'R,4'E)-2'-azido-3-O-tert-butyldimethylsilyl-3'-hydroxy-4'-octadecenoyl>-4-(isopropyl)-2-oxazolidinone 
• 103348-49-8 2-azido-sphingosine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 114275-42-2 (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-1-(pivaloyloxy)-4-octadecen 
• 157639-67-3 (2S,3R,4E)-2-azido-1-benzoyloxy-octadec-4-ene-3-ol 
• 3163-37-9 (E)-hexadec-2-enal 
• 117606-35-6 (4S)-3-<(2'S,3'R,4'E)-2'-bromo-3'-hydroxy-4-(isopropyl)-4'-octadecenoyl>-2-oxazolidinone 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 114275-41-1 (2S,3R,4E)-2-Azido-1-(pivaloyloxy)-4-octadecen-3-ol 
• 104826-27-9 <2(R),3(R),4E>-1,3-O-isopropylidene-4-octadecene-1,2,3-triol 

Downstream Products

• 137905-29-4 (2S,3R,4E)-2-amino-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-ol 
• 162019-91-2 (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-1,2-(2,4-dinitrophenyl)imino-4-octadecene 
• 157639-70-8 (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(2,4-dinitrophenyl)amino-4-octadecen-1-ol 
• 103348-49-8 2-azido-sphingosine 
• 157639-71-9 (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(2,4-dinitrophenyl)amino-1-iodo-4-octadecene 
• 162020-01-1 (2S,3R,4E)-1-(5a-carba-β-D-glucopyranosylthio)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol 
• 162020-00-0 (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(2,4-dinitrophenylamino)-1-(2,3,4,6-tetra-O-benzoyl-5a-carba-β-D-glucopyranosylthio)-4-octadecene 
• 162020-11-3 (2S,3R,4E)-3-tert-butyldimethylsilyloxy-2-(2,4-dinitrophenyl)-amino-1-(3,4-O-isopropylidene-5a-carba-β-D-galactopyranosylamino)-4-octadecene 
• 162020-06-6 (2S,3R,4E)-1-(4,6-O-benzylidene-5a-carba-β-D-glucopyranosylamino)-3-(tert-butyldimethylsilyloxy)-2-(2,4-dinitrophenyl)amino-4-octadecene 
• 162020-07-7 (2S,3R,4E)-1-(5a-carba-β-D-glucopyranosylamino)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol 
• 162119-30-4 (2S,3R,4E)-1-(5a-carba-β-D-galactopyranosylamino)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol 
• 157639-65-1 (2S,3R,4E)-3-tert-butyldimethylsilyloxy-1-<2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamino>-2-(2,4-dinitrophenyl)amino-4-octadecene 

Relevant articles and documents

STUDIES ON MORPHOLINOSPHINGOLIPIDS: POTENT INHIBITORS OF GLUCOSYLCERAMIDE SYNTHASE

Synthetic 1-morpholino-1-deoxyceramides were designed to inhibit glucosylceramide synthase.The most potent inhibitor 2a possesses the unnatural R,R-configuration of D-threo-sphingosine.

Synthesis of 5a-Carba-&β-D-glycosylceramide Analogs Linked by Imino, Ether and Sulfide Bridges

Carbocyclic analogs of glycoceramides, (2S,3R,4E)-1-(5a-carba-β-D-glycopyranosyl)-2-(hexadecanoylamino)-4-octadecen-3-ols E-3 - E-6, linked by imino, ether and sulfide bridges, were synthesized by coupling of aziridines, as the sphingosine precursors, wit

Total synthesis of globotriaosylceramide (Gb3) and lysoglobotriaosylceramide (lysoGb3)

We have recently reported a highly efficient and stereocontrolled synthesis of globotriaosylceramide (Gb3, 1) in optically pure form.Key to our synthetic strategy was the implementation of the two-stage activation of thioglycosides for formatio