3530-53-8

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3S,4R)-2-Amino-1,3,4-icosanetriol is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs targeting specific biological pathways.
Used in Cosmetic Industry:
In the cosmetic industry, (2S,3S,4R)-2-Amino-1,3,4-icosanetriol is used as an active ingredient for its potential moisturizing and skin-conditioning properties. Its ability to interact with skin proteins and lipids may contribute to improved skin hydration and overall skin health.
Used in Research and Development:
(2S,3S,4R)-2-Amino-1,3,4-icosanetriol is used as a research tool for studying the structure and function of biological molecules. Its unique stereochemistry makes it an interesting candidate for understanding the role of stereoselectivity in molecular recognition and biological activity.
Used in Chemical Synthesis:
As a versatile organic compound, (2S,3S,4R)-2-Amino-1,3,4-icosanetriol can be used as a starting material or intermediate in the synthesis of other complex molecules, such as natural products, pharmaceuticals, and specialty chemicals.

Upstream product

• 164988-76-5 (2S,3S,4R)-2-azido-1,3,4-tri-O-benzyl-1,3,4-eicosanetriol 
• 1335002-13-5 (2S,3S,4R)-2-aminoicosane-1,3,4-triol TFA salt 

Relevant academic research and scientific papers

A facile synthesis of D-ribo-C20-phytosphingosine and its C2 epimer from D-ribose

A facile synthetic route to D-ribo-C20-phytosphingosine 31 and its C2 epimer 32 is described. The Overman rearrangement of allylic trichloroacetimidates derived from the known ribose derivative 7 has been used as the key step. The subsequent functional group interconversions in rearranged products 14 and 15 followed by Wittig olefination, Pd/C-mediated reduction and the removal of protecting groups successfully constructed the final molecules.

Synthesis of Sphingosines, 11 - Convenient Synthesis of Phytosphingosine and Sphinganine from D-Galactal and D-Arabitol

3,4,6-Tri-O-benzyl-D-galactal (3) was directly converted into 3,4,6-tri-O-benzyl-2-deoxy-D-galactose (5).Wittig reaction of 5 with alkyltriphenylphosphonium salts in the presence of n-butyllithium as the base afforded olefins 6a, b which could be readily transformed into phytosphingosines 1a, b via different routes; (i) at first group introduction and then double bond and protective group removal, and azido group generation via hydrogenation; (ii) 2-O-mesylation, then double bond and benzyl group removal via hydrogenation, and finally nitrogen introduction; (iii) selective double bond hydrogenation, then nitrogen introduction, and finally benzyl group removal and amino group generation via hydrogenation.Wittig reaction of 5 with alkyltriphenylphosphonium salt in the presence of potassium tert-butoxide as the base afforded diene 7a which proved to be a convenient precursor for sphinganine syntheses; thus, 2-O-mesylation, then double bond and benzyl group removal via hydrogenation and 1,3-O-acetylation, and finally nitrogen introduction and de-O-acetylation afforded 23a.Based on the convenient transformation of D-arabitol into the 1,3-O-benzylidene derivative 25 a further phytosphingosine synthesis is outlined. - Key Words: Phytosphingosine / Sphinganine / Galactal / 2-Deoxy-D-galactose / D-Arabitol / Carbohydrates