Approaches to the preparation of sphinganines

Howell, Amy R.; So, Regina C.; Richardson, Stewart K.

doi:10.1016/j.tet.2004.09.056

Cited by 74 publications

(11 citation statements)

References 67 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The history of the syntheses of the sphinganines has been reviewed13 and covers the period from the first synthesis in 1951 up to 2004, and many other syntheses have appeared subsequent to this review 14. The earlier syntheses of sphinganines tended to be nonselective, which gave mixtures of diastereomers that needed to be separated and enantiomers that needed to be resolved.…”

Section: Introductionmentioning

confidence: 99%

A General Synthesis of Sphinganines through Multicomponent Catalytic Asymmetric Aziridination

Mukherjee¹,

Zhou²,

Gupta³

et al. 2014

Eur J Org Chem

View full text Add to dashboard Cite

A catalytic asymmetric synthesis of all four stereoisomers of sphinganine is described starting from hexadecanal. Utilizing either the (R) or (S) enantiomer of a BOROX catalyst, a multicomponent reaction of this aldehyde with an amine and ethyl diazoacetate gives rise to enantiomeric aziridine‐2‐carboxylates. Access to all diastereomers of sphinganine is realized upon ring opening of the enantiopure aziridine‐2‐carboxylate at the C‐3 position by direct SN2 attack of an oxygen nucleophile, which occurs with inversion of configuration and by ring expansion of an N‐acyl aziridine to an oxazolidinone and then hydrolysis. Overall, this process results in the formal ring opening of the aziridine with an oxygen nucleophile with retention of configuration.

show abstract

Section: Introductionmentioning

confidence: 99%

A General Synthesis of Sphinganines through Multicomponent Catalytic Asymmetric Aziridination

Mukherjee¹,

Zhou²,

Gupta³

et al. 2014

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…2 In contrast, the V3 loop interacts with GalCer with a high affinity, so that this major intestinal GSL has long been recognized as a real receptor for HIV-1. 3 This and other findings have stimulated the research in the synthesis of glycosphingolipids, 1a,b,4 ceramides 4a,b and sphingosines 4a, 5 as an alternative to the natural sources. 6 The current retrosynthetic analysis reveal three important steps in the syntheses of b-GalCer 4: (i) glycosylation of the sphingosine moiety, (ii) N-acylation with the fatty acid and finally (iii) elimination of the protecting groups (Fig.…”

Section: Introductionmentioning

confidence: 99%

Stannyl ceramides as efficient acceptors for synthesising β-galactosyl ceramides

et al. 2008

View full text Add to dashboard Cite

show abstract

“…Due to the lack of a readily available natural sources and the high biological importance of sphingolipid analogues, their synthesis has been the subject of numerous studies [16]. The key step for the synthesis is the stereoselective construction of the 2-amino-1,3-diol moiety of the molecules.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols

Bajtel

Raji

Haukka

et al. 2021

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

A library of pinane-based 2-amino-1,3-diols was synthesised in a stereoselective manner. Isopinocarveol prepared from (−)-α-pinene was converted into condensed oxazolidin-2-one in two steps by carbamate formation followed by a stereoselective aminohydroxylation process. The relative stereochemistry of the pinane-fused oxazolidin-2-one was determined by 2D NMR and X-ray spectroscopic techniques. The regioisomeric spiro-oxazolidin-2-one was prepared in a similar way starting from the commercially available (1R)-(−)-myrtenol (10). The reduction or alkaline hydrolysis of the oxazolidines, followed by reductive alkylation resulted in primary and secondary 2-amino-1,3-diols, which underwent a regioselective ring closure with formaldehyde or benzaldehyde delivering pinane-condensed oxazolidines. During the preparation of 2-phenyliminooxazolidine, an interesting ring–ring tautomerism was observed in CDCl3.

show abstract

Approaches to the preparation of sphinganines

Cited by 74 publications

References 67 publications

A General Synthesis of Sphinganines through Multicomponent Catalytic Asymmetric Aziridination

A General Synthesis of Sphinganines through Multicomponent Catalytic Asymmetric Aziridination

Stannyl ceramides as efficient acceptors for synthesising β-galactosyl ceramides

Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols

Contact Info

Product

Resources

About