79409-46-4

Basic information

• Product Name: SECOLOGANIN ETHYLENE ACETAL TETRAACETATE
• Synonyms: SECOLOGANIN ETHYLENE ACETAL TETRAACETATE
• CAS NO: 79409-46-4
• Molecular Formula: C₂₇H₃₆O₁₅
• Molecular Weight: 600.57
• Mol File: 79409-46-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 632.2°C at 760 mmHg
• Flash Point: 263.8°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 6.83E-16mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: SECOLOGANIN ETHYLENE ACETAL TETRAACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: SECOLOGANIN ETHYLENE ACETAL TETRAACETATE(79409-46-4)
• EPA Substance Registry System: SECOLOGANIN ETHYLENE ACETAL TETRAACETATE(79409-46-4)

Safety Data

• Hazardous Substances Data: 79409-46-4(Hazardous Substances Data)

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

• 19351-63-4 secologanin 
• 27856-66-2 O,O,O,O-tetraacetylsecologaninn 
• 107-21-1 ethylene glycol 
• 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 
• 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 

Downstream Products

• 27856-66-2 O,O,O,O-tetraacetylsecologaninn 
• 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 
• 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 

Relevant articles and documents

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.

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.