169238-10-2

Upstream product

• 161459-65-0 phenyl (2S,3R)-2-benzyloxy-3-hydroxy-5-trimethylsilylpent-4-ynoate 
• 169238-09-9 (2R,3R)-2-benzyloxy-5-trimethylsilylpent-4-yne-1,3-diol 
• 161459-66-1 (4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane 

Downstream Products

• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 161459-67-2 (4R,5R)-5-benzyloxy-4-(pentadec-1-ynyl)-2,2-dimethyl-1,3-dioxane 

Relevant academic research and scientific papers

Use of heterocycles as chiral ligands and auxiliaries in asymmetric syntheses of sphingosine, sphingofungins B and F

D-erythro-Sphingosine and its derivatives (dihydrosphingosine, cissphingosine, etc.), sphingofungins B and F have been synthesized from simple achiral compounds using heterocyclic compounds as key chiral ligands and auxiliaries. 5-Benzyloxy-4-ethynyl-2,2-dimethyl-1,3-dioxane (5 or 5- ent), a key intermediate for the synthesis of sphingosine family, was prepared from 1-trimethylsilylpropinal and ketene silyl acetal 4 using a Sn(OTf)2-chiral ligand 1 or 1-ent-catalyzed asymmetric aldol reaction. Sphingosine and its derivatives were readily prepared from 5 according to standard transformation. The chiral hydrophobic side chain (6) of sphingofungin B was synthesized using a catalytic asymmetric aldol reaction using chiral ligand 1-ent. Another key step in the total synthesis of sphingofungin B was a condensation of chiral aldehyde 7 and chiral heterocycle 2. Similarly, the reaction of chiral aldehyde 8 with heterocycle 3 was a key step for the synthesis of sphingofungin F. Highly diastereoselective reactions proceeded smoothly in both cases to afford the corresponding adducts in high yields.

Enantioselective Syntheses of D-erythro-Sphingosine and Phytosphingosine from Simple Achiral Aldehydes Using Catalytic Asymmetric Aldol Reactions as Key Steps

D-erythro-sphingosine and phytosphingosine were prepared from simple achiral aldehydes, trimethylsilylproynal and acrolein, by using chiarl tin(II) Lewis acid-catalyzed asymmetric aldol reactions as key steps.