98048-64-7

Upstream product

• 14663-13-9 DL-erythro-2-Benzylamino-3-hydroxy-octadecansaeure-⁽¹⁾ 
• 100-46-9 benzylamine 
• 4444-84-2 (+/-)-threo-2,3-epoxy-octadecanoic acid 
• 81306-31-2 (2R,3R)-2,3-epoxyoctadecan-1-ol 
• 3173-56-6 benzyl isothiocyanate 
• 100-52-7 benzaldehyde 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 97975-08-1 1-<(N-benzylcarbamoyl)oxy>-trans-2,3-epoxyoctadecane 
• 102874-89-5 (2S,3R)-2-benzylideneamino-octadec-4t-ene-1,3-diol 
• 103048-40-4 (+/-)-erythro-2-benzoylamino-3-hydroxy-octadecanoic acid methyl ester 
• 103048-40-4 (+/-)-threo-2-benzoylamino-3-hydroxy-octadecanoic acid methyl ester 

Downstream Products

• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 
• 6036-76-6 (2R,3S)-2-aminooctadecane-1,3-diol 
• 3102-56-5 dihydrosphingosine 
• 13031-64-6 N-acetyldihydrosphingosine 

Relevant academic research and scientific papers

Process for preparing 2-amino-1, 3-alkanediol or a derivative thereof, process for preparing optically active dihydrosphingosine derivatives and intermediates used in that process

A process for preparing an optically active dihydrosphingosine derivative, comprising reducing a (2R,3R)-2-amino-3-hydroxyalkanoic acid derivative represented by formula (III): wherein R3represents a straight-chain alkyl group having 7 to 21 carbon atoms; and R4represents an amino group protecting group,(e.g., (2R,3R)-2-benzylamino-3-hydroxyoctadecanoic acid) with sodium tetrahydroborate in the presence of an acid. The process of the invention makes it feasible to produce an optically active dihydrosphingosine at high optical purity and provides a simple process that is safe and easy to industrialize.

Directed Openings of 2,3-Epoxy Alcohols via Reactions with Isocyanates: Synthesis of (+)-erythro-Dihydrosphingosine

Two methods for the synthesis of 2-(N-alkylamino) 1,3-diols from 2,3-epoxy alcohols are described.In one procedure (method A) an epoxyurethane (5, 8, 11, 14, 16) prepared from the corresponding epoxy alcohol by standard procedures is cyclized to a 2-oxazolidinone derivative (6, 9, 12, 15, 17) in 81-90percent yield by treatment with NaH in THF or NaOMe in MeOH.The second procedure (method B) involves treatment of the epoxy alcohol (4, 7, 10, 13, 24) with benzyl isocyanate, an NH3 synthetic equivalent, and NaH in THF at reflux.Hydrolysis of the crude isoxazolidinones by exposure to LiOH in EtOH at reflux smoothly affords 2-(N-benzylamino) 1,3-diols (22, 23, 30, 31) in 68-72percent overall yield.These procedures are highly regioselective; products resulting from intramolecular addition of the urethane nitrogen atom to the epoxide β-position were not detected.This methodology was applied to a short, highly stereoselective synthesis of (+)-erythro-dihydrosphingosine (26) from palmitic aldehyde ( 47-54percent overall yield).