140408-14-6

Basic information

• Product Name: N-[(1S,2R)-2-Hydroxy-1-(hydroxyMethyl)heptadecyl]carbaMic Acid 1,1-DiMethylethyl Ester
• Synonyms: N-[(1S,2R)-2-Hydroxy-1-(hydroxyMethyl)heptadecyl]carbaMic Acid 1,1-DiMethylethyl Ester;N-tert-Butyloxycarbonyl-D-erythro-dihydro-D-sphingosine
• CAS NO: 140408-14-6
• Molecular Formula: C₂₃H₄₇NO₄
• Molecular Weight: 401.62358
• Product Categories: Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators;Glycerols, Fatty Acid Derivatives & Lipids
• Mol File: 140408-14-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: N-[(1S,2R)-2-Hydroxy-1-(hydroxyMethyl)heptadecyl]carbaMic Acid 1,1-DiMethylethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(1S,2R)-2-Hydroxy-1-(hydroxyMethyl)heptadecyl]carbaMic Acid 1,1-DiMethylethyl Ester(140408-14-6)
• EPA Substance Registry System: N-[(1S,2R)-2-Hydroxy-1-(hydroxyMethyl)heptadecyl]carbaMic Acid 1,1-DiMethylethyl Ester(140408-14-6)

Safety Data

• Hazardous Substances Data: 140408-14-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Protected D-erythro-C18-Dihydro-D-sphingosine (D449400). Biosynthetic precursor of Sphingosine. Inhibits protein kinase C.

Upstream product

• 131606-77-4 (2S,3R)-2-[(tert-butoxycarbonyl)amino]-1,2-O-N-isopropylideneoctadecane-1,3-diol 
• 122709-20-0 N-(tert-butoxycarbonyl)-L-serine N'-methoxy-N'-methylamide 
• 244023-85-6 (S)-3-(tert-butoxycarbonylamino)-1,5-dioxaspiro[3.2]hexane 
• 114301-34-7 tert-butyl (S)-4-((R)-1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 115464-03-4 tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 116467-63-1 N-tert-butyloxycarbonylsphingosine 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 115464-01-2 (4S,1'R)-4-(1'-Hydroxy-2'-hexadecinyl)-2,2-dimethyl-3-oxazolidincarbonsaeure-tert-butylester 
• 213338-89-7 (S)-3-(tert-butoxycarbonylamino)-2-methyleneoxetane 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 620161-22-0 2(S)-[(1(R)-phenylethyl)amino]octadecane-1,3-diol 
• 437609-37-5 (2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one 

Downstream Products

• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 

Relevant articles and documents

Studies on the inhibition of sphingosine-1-phosphate lyase by stabilized reaction intermediates and stereodefined azido phosphates

Two kinds of inhibitors of the PLP-dependent enzyme sphingosine-1-phosphate lyase have been designed and tested on the bacterial (StS1PL) and the human (hS1PL) enzymes. Amino phosphates 1, 12, and 32, mimicking the intermediate aldimines of the catalytic process, were weak inhibitors on both enzyme sources. On the other hand, a series of stereodefined azido phosphates, resulting from the replacement of the amino group of the natural substrates with an azido group, afforded competitive inhibitors in the low micromolar range on both enzyme sources. This similar behavior represents an experimental evidence of the reported structural similarities for both enzymes at their active site level. Interestingly, the anti-isomers of the non-natural enantiomeric series where the most potent inhibitors on hS1PL.

Efficient synthesis of enantiomerically pure 2-acylaziridines: Facile syntheses of N-Boc-safingol, N-Boc-D-erythro-sphinganine, and N-Boc-spisulosine from a common intermediate

Various enantiomerically pure 2-acylaziridines were prepared efficiently from the corresponding aziridine-2-carboxylate via Weinreb's amide and the subsequent treatment of organometallic compounds. The carbonyl group of those 2-acylaziridines was stereose

Synthesis of Sphingosine Relatives, XIV. A New Synthesis of Symbioramide, a Ca(++)-ATPase Activator from Symbiodinium sp.

Symbioramide was synthesized from D-erythro-dihydrosphingosine (19) and (R,E)-2'-tert-butyldimethylsilyloxy-3'-octadecenoic acid (14), which was prepared from (E)-2-octadecen-1-ol (4) by employing the Sharpless asymmetric epoxidation.The (2S,2'S,3R,3'E)-isomer 28 of 1 was also synthesized to further confirm the structure of 1. - Key Words: Ca(++)-ATPase activator / Ceramides / Marine natural products / Sphingosines / Symbioramide