161459-65-0

Upstream product

• 2975-46-4 3-(trimethylsilyl)prop-2-yn-1-al 

Downstream Products

• 161459-67-2 (4R,5R)-5-benzyloxy-4-(pentadec-1-ynyl)-2,2-dimethyl-1,3-dioxane 
• 161459-66-1 (4S,5S)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane 
• 169238-10-2 (4R,5R)-5-benzyloxy-4-ethynyl-2,2-dimethyl-1,3-dioxane 
• 169238-09-9 (2R,3R)-2-benzyloxy-5-trimethylsilylpent-4-yne-1,3-diol 

Relevant academic research and scientific papers

Catalytic asymmetric syntheses of antifungal sphingofungins and their biological activity as potent inhibitors of serine palmitoyltransferase (SPT)

Unambiguous synthetic routes to sphingofungins B and F and to their stereoisomers have been developed based on the tin(II)-catalyzed asymmetric aldol reaction (Chiral Lewis Acid-Controlled Synthesis (CLAC Synthesis)). Efficient enantioselective synthesis using a catalytic amount of a chiral source as well as the effectiveness of this strategy for the synthesis of the sphingofungin family have been successfully demonstrated. Using the stereoisomers of sphingofungin B synthesized, the relevance of its stereochemistry to its SPT inhibitory activity has been revealed.

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.

The Asymmetric Synthesis of Sphingofungin F and the Determination of Its Stereochemistry

The asymmetric synthesis of sphingofungin F has been achieved and its stereochemistry has been determined. Its structure, including the absolute configuration of the chiral centers, was found to be similar to that of sphingofungin B or myriocin. The synth

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.