89103-54-8

Upstream product

• 76235-25-1 3'-O-acetyl-3'-epigomphoside 
• 52080-34-9 1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-D-arabino-hex-1-enitol 
• 87713-47-1 3,4-di-O-benzoyl-6-deoxy-α-D-arabino-hexopyranos-2-ulosyl bromide 
• 76235-22-8 2',3'-OO-isopropylidenegomphoside 
• 866941-35-7 C₄₃H₅₀O₁₁ 
• 866941-37-9 C₃₆H₄₄O₉ 
• 88972-30-9 3'-didehydrogomphoside 

Relevant academic research and scientific papers

A concise and general method for doubly attaching 2-ketosugars to aglycon diols: Synthesis of the gomphosides and spectinomycin

(Chemical Equation Presented) Spectinomycin and the gomphosides: Use of 6-deoxyhexulosyl derivatives of D-glucose in Ag2CO 3-mediated glycosylation of gomphogenin and actinamine has allowed the first syntheses of cardiac glycosides with ring A-annulated sugar components (see picture; Bz = benzoyl) and an alternate synthesis of the antibiotic spectinomycin.

Cardenolide Glycosides of the Asclepiadaceae. New Glycosides from Asclepias fruticosa and the Stereochemistry of Uscharin, Voruscharin and Calotoxin

Eight new cardenolide glycosides, 19-deoxyuscharin (1b), 4'β-hydroxygomphoside (1k), 3'-didehydrogomphoside (1d), 3'-epigomphoside (1e), 3'-epiafroside (2e), 3'-epigomphoside 3'-acetate (1f), 3'-didehydroafroside (2d), and 3'-epiafroside 3'-acetate (2f), have been isolated from Asclepias fruticosa R.Br.The structures of all new compounds were established by spectral comparisons with known compounds.The chirality of C-3' of uscharin (3b), voruscharin, and 19-deoxyuscharin (1b) is proposed to be S.By comparison with 4'β-hydroxygomphoside (1k), the β configuration of the 4'-hydroxy group of calotoxin (3k) (from Calotropis procera) has been established.

Stereochemistry of the Hexosulose in Cardenolide Glycosides of the Asclepiadaceae

The 4,6-dideoxyhexosulose moiety of gomphoside (1) and afroside (2) has been shown to have the 1'S,2'S,3'R,5'R configuration.Formation of 2',3'-OO-isopropylidene derivatives establishes that the hydroxy-group at C-3', which is axial, is cis to that at C-2'.The latter group is cis to the anomeric C-1' hydrogen, as shown by nuclear Overhauser enchancement measurements.Chemical and 1H and 13C n.m.r. data have been used to show that the same chirality at carbons 1', 2', and 5' is present in the following glycisides from plants of the Asclepiadaceae family: calactin (3), syriobioside (10), desglucosyrioside (11), syrioside (12), uscharidin (5), calotoxin (9), uscharin (7), and voruscharin (8).