79409-46-4

Usage

InChI:InChI=1/C27H36O15/c1-7-17-18(10-21-34-8-9-35-21)19(25(32)33-6)11-37-26(17)42-27-24(40-16(5)31)23(39-15(4)30)22(38-14(3)29)20(41-27)12-36-13(2)28/h7,11,17-18,20-24,26-27H,1,8-10,12H2,2-6H3/t17-,18+,20+,22+,23-,24+,26+,27-/m1/s1

Upstream product

• 20667-19-0 methyltriphenylphosphonium iodide 
• 79420-93-2 (4S,5S,6S)-4-[1,3]Dioxolan-2-ylmethyl-5-formyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 
• 108-24-7 acetic anhydride 
• 79409-45-3 Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate 
• 27856-66-2 O,O,O,O-tetraacetylsecologaninn 
• 107-21-1 ethylene glycol 
• 19351-63-4 secologanin 

Downstream Products

• 60077-47-6 (4aS,5R,6S)-3-Methoxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one 
• 549-84-8 β-yohimbine 
• 2671-57-0 (+)-yohimbinone 
• 146-48-5 Yohimbine 
• 483-04-5 ajmalicine 
• 297131-94-3 (1R,2R,6R)-2-[1,3]Dioxolan-2-ylmethyl-6-hydroxy-3-{[2-(1H-indol-3-yl)-ethylamino]-methyl}-cyclohex-3-enecarboxylic acid methyl ester 
• 120132-02-7 (1R,2R,6R)-2-[1,3]Dioxolan-2-ylmethyl-3-formyl-6-hydroxy-cyclohex-3-enecarboxylic acid methyl ester 
• 16049-28-8 antirhine 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 79409-47-5 Methyl (2S,3S,4S,9S)-3-(1,2-dihydroxyethyl)-4-(1,3-dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate 
• 79409-49-7 Methyl (1S,4aS,6R,9S,9aS)-4a,5,6,8,9,9a-hexahydro-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-6,9-epoxy-1H-pyrano<3,4-d>oxepine-4-carboxylate 
• 102436-08-8 Methyl (1S,4aS,6RS,8S,8aS)-1,4a,5,6,8,8a-hexahydro-6-hydroxy-8-(hydroxymethyl)-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)pyrano<3,4-c>pyran-4-carboxylate 
• 27856-66-2 O,O,O,O-tetraacetylsecologaninn 

Relevant academic research and scientific papers

Semi-synthesis of secologanin analogues

Secologanin, a complex iridoid terpene natural product, was derivatized at the vinyl and ester functional groups using cross-metathesis and transesterification methodology, respectively.

Enantiospecific synthesis of (-)-3-iso-19,20-dehydro-β-yohimbine from secologanin: A route to normal and pseudo stereoisomers of yohimbine

Hydrolysis of secologanin ethylene acetal at pH 7 resulted in stereoselective aldol cyclisation to a cyclohexene aldehyde, which, on reductive amination and cyclisation with tryptamine afforded (-)-3-iso-19,20- dehydro-β-yohimbine, converted into various normal and pseudo isomers of yohimbine. (C) 2000 Elsevier Science Ltd.

Biomimetic synthesis of monoterpenoid indole alkaloids from aglucones of secologanin derivatives: pH controlled product selectivity

Variation of the pH for hydrolysis of secologanin derivatives with β-glucosidase controls rearrangement of the aglucone to afford different products, and hence stercoselective syntheses of heteroyohimbine, yohimbine and Aspidosperma-type alkaloids; with baker's yeast chemoselective reduction can also be achieved to give a precursor for antirhine and related alkaloids.

Hydrolysis and Selective Reduction with Yeast: Enantiospecific Synthesis of Antirhine from Secologanin

Glucoside hydrolysis and chemoselective reduction of secologanin ethylene acetal 2 with baker's yest affords a C-1 reduced aglucone 4 from which (+)-antirhine 8 is obtained in a four-step sequence.

Iridoids, XXI. - Synthesis of Secologanin

Acid-catalyzed reaction of natural secologanin (1) with ethylene glycol to 5a, followed by acetylation gave the peracetylated acetal 5b in almost quantitative yield.Oxidation of 5b with equimolar or catalytic amounts of osmium tetraoxide afforded stereoselectively the diol 6 as main product (31percent resp. 28percent) besides recovered starting material. 5b was cleaved with lead tetraacetate to give 96percent of the aldehyde 10.Reaction of 10 with triphenylphosphonio-methanide led to the labelled secologanin derivative -5b and the pyran 12 in a 27percent and 52percent yield, respectively.Acid-catalyzed transacetalization of -5b to -5c, base-catalyzed solvolysis of the acetate groups to -5d and subsequent acid-catalyzed cleavage of the acetal gave secologanin (-1).To determine its configuration at C-9, 6 was transformed via 8a to the tricyclic system 8d, which was independently synthesized via a photocycloaddition of the galactose derivative 13 and diformylacetate 14.