120005-55-2

Upstream product

• 115464-01-2 (4S,1'R)-4-(1'-Hydroxy-2'-hexadecinyl)-2,2-dimethyl-3-oxazolidincarbonsaeure-tert-butylester 
• 785828-30-0 tert-butyl (4S)-4-[1-hydroxyhexadec-2-ynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 765-13-9 pentadec-1-yne 
• 139009-66-8 (S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 

Relevant academic research and scientific papers

Syntheses of 3-C-methylceramides

We report on the synthesis of a series of 3-C-methylceramide derivatives 2a,b, 12a,b, 13a,b, and 14a,b. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Synthesis and evaluation of sphingosine analogues as inhibitors of sphingosine kinases

Sphingolipid-metabolizing enzymes control the critical balance of the cellular levels of sphingolipids, including the apoptotic inducing ceramide (Cer) and the proliferative inducing sphingosine 1-phosphate (S1P). The production of S1P, catalyzed by the action of sphingosine kinases (SPHKs), is known to be critical for many cellular processes. However, it is suggested that SPHK, and/or its catalytic product S1P, plays critical roles in various diseases including autoimmune diseases, cancer, and allergies. However, there is a great limitation of specific pharmacological inhibitors for SPHKs. In this paper, we describe a novel and stereoselective method of synthesizing SPHKs inhibitors. We generated a number of novel compounds and identified a number of specific inhibitors of human SPHKs. These compounds demonstrated inhibition of SPHKs at micromolar concentrations, making them more potent than dimethylsphingosine (DMS), a wellknown inhibitor of SPHKs. In particular, one of the inhibitors was found to be selective toward a particular isoform of SPHK.

Facile and efficient addition of terminal alkynes to benzotriazole esters: Synthesis of d-erythro-sphingosine using ynones as the key intermediate

From the perspective of synthesis, ynones are compounds of considerable interest because of their occurrence in a wide variety of biologically active molecules and as key synthetic intermediates. In this context, a facile and highly efficient synthesis of ynones was developed based on the high reactivity of benzotriazole esters formed in situ. Lithium acetylides can alkylate various carboxylic acids in yields ranging from 60% to 92%. To determine whether our methodology is useful for synthesising complex and biologically relevant molecules, we synthesise d-erythro-sphingosine in four steps and with 33% overall yield from l-serine.