36597-51-0

Basic information

• Product Name: gomphoside
• Synonyms: gomphoside;14-Hydroxy-3β,2α-[[[(2S,3S,4R,6R)-tetrahydro-3,4-dihydroxy-6-methyl-2H-pyran]-2,3-diyl]bis(oxy)]-5α-card-20(22)-enolide;2α,3β-[[(2S,3S,4R,6R)-Tetrahydro-3,4-dihydroxy-6-methyl-2H-pyran-3,2-diyl]bisoxy]-14-hydroxy-5α-card-20(22)-enolide
• CAS NO: 36597-51-0
• Molecular Formula: C29H42O8
• Molecular Weight: 518.643
• Mol File: 36597-51-0.mol

Chemical Properties

• Boiling Point: 699.8°Cat760mmHg
• Flash Point: 229.3°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 1.22E-22mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: gomphoside(CAS DataBase Reference)
• NIST Chemistry Reference: gomphoside(36597-51-0)
• EPA Substance Registry System: gomphoside(36597-51-0)

Safety Data

• Hazardous Substances Data: 36597-51-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C29H42O8/c1-15-10-23(30)29(33)25(35-15)36-22-13-26(2)17(12-21(22)37-29)4-5-20-19(26)6-8-27(3)18(7-9-28(20,27)32)16-11-24(31)34-14-16/h11,15,17-23,25,30,32-33H,4-10,12-14H2,1-3H3/t15-,17+,18-,19+,20-,21+,22+,23-,25+,26+,27-,28?,29+/m1/s1

Upstream product

• 76235-22-8 2',3'-OO-isopropylidenegomphoside 
• 88972-30-9 3'-didehydrogomphoside 
• 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 
• 866941-35-7 C₄₃H₅₀O₁₁ 
• 866941-37-9 C₃₆H₄₄O₉ 

Relevant articles and documents

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.

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).