Glycoside mimics from glycosylamines: Recent progress

C Nicolas, OR Martin - Molecules, 2018 - mdpi.com
Glycosylamines are valuable sugar derivatives that have attracted much attention as
synthetic intermediates en route to iminosugar-C-glycosyl compounds. Iminosugars are …

Marine cytotoxic jaspine B and its stereoisomers: Biological activity and syntheses

M Martinková, J Gonda - Carbohydrate Research, 2016 - Elsevier
Conformationally constrained sphingolipids such as anhydrophytosphingosines
represented by jaspine B (also known as pachastrissamine) and its stereoisomers have …

Synthesis and biological evaluation of 2-epi-jaspine B analogs as selective sphingosine kinase 1 inhibitors

H Yang, Y Li, H Chai, T Yakura, B Liu, Q Yao - Bioorganic Chemistry, 2020 - Elsevier
Epi-jaspine B is an isomer of the natural product jaspine B and shows certain selectivity for
SphK1 and potent antitumor activity. Based on the crystal structure of SphK1, we …

Stereoselective Synthesis of Iminosugar‐C‐Glycosides through Addition of Organometallic Reagents to Ntert‐Butanesulfinyl Glycosylamines: A Comprehensive …

D Kamzol, M Neuville, C Cocaud… - European Journal of …, 2023 - Wiley Online Library
A comprehensive study of the preparation and reactivity of N‐tert‐butanesulfinyl
glycosylamines with simple Grignard and organo lithium reagents in batch vs. continuous …

Total synthesis of pachastrissamine together with its 4-epi-congener via [3, 3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation

M Martinková, E Mezeiová, M Fabišíková, J Gonda… - Carbohydrate …, 2015 - Elsevier
Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-
congener 5 from easily available dimethyl l-tartrate and/or l-arabinose, is described. The key …

Synthesis of pachastrissamine (jaspine B) and its derivatives by the late-stage introduction of the C-2 alkyl side-chains using olefin cross metathesis

Y Yoshimitsu, J Miyagaki, S Oishi, N Fujii, H Ohno - Tetrahedron, 2013 - Elsevier
An improved divergent synthesis of the four diastereomers of pachastrissamine from
Garner's aldehyde has been reported. The common intermediate was synthesized by an …

Total synthesis of (−)-jaspine B and its 4-epi-analogue from d-xylose

M Martinkova, E Mezeiova, J Gonda, D Jackova… - Tetrahedron …, 2014 - Elsevier
The total synthesis of the HCl salts of (−)-jaspine B ent-1 and its 4-epi-congener ent-4 was
accomplished starting from the common template 13 derived from d-xylose. The cornerstone …

A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N, O, O, O-tetra-acetyl d-lyxo-phytosphingosine

GS Rao, BV Rao - Tetrahedron letters, 2011 - Elsevier
The highly stereoselective Grignard addition on chiralimine 8 and opening of chiral epoxide
9 with Grignard reagent have been used as key steps in the stereoselective synthesis of …

A common approach to the total synthesis of L-arabino-, L-ribo-C18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from D-mannose

M Martinková, K Pomikalová, J Gonda, M Vilková - Tetrahedron, 2013 - Elsevier
A common strategy for the total syntheses of the protected l-arabino-and l-ribo-C 18-
phytosphingosine (8 and 9, respectively), HCl salts of ent-2-epi-jaspine B (ent-6) and 3-epi …

Stereoselective synthesis of (−)-conduramine C-1 and (−)-conduramine D-1

A Rajender, BV Rao - Tetrahedron Letters, 2013 - Elsevier
A highly stereoselective approach to aminocyclohexenetriols conduramine C-1 1 and
conduramine D-1 2 has been described. Conduramines are structural units of some …