20586-11-2

Basic information

• Product Name: (1S)-1α-(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyloxy)-6α-acetoxy-7α-methyl-1,4aα,5,6,7,7aα-hexahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester
• Synonyms: (1S)-1α-(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyloxy)-6α-acetoxy-7α-methyl-1,4aα,5,6,7,7aα-hexahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester;(1S)-6α-(Acetyloxy)-1,4aα,5,6,7,7aα-hexahydro-7α-methyl-1α-[(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)oxy]cyclopenta[c]pyran-4-carboxylic acid methyl ester;Loganin pentaacetate
• CAS NO: 20586-11-2
• Molecular Formula: C₂₇H₃₆O₁₅
• Molecular Weight: 600.56574
• Mol File: 20586-11-2.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S)-1α-(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyloxy)-6α-acetoxy-7α-methyl-1,4aα,5,6,7,7aα-hexahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-1α-(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyloxy)-6α-acetoxy-7α-methyl-1,4aα,5,6,7,7aα-hexahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester(20586-11-2)
• EPA Substance Registry System: (1S)-1α-(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyloxy)-6α-acetoxy-7α-methyl-1,4aα,5,6,7,7aα-hexahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester(20586-11-2)

Safety Data

• Hazardous Substances Data: 20586-11-2(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 29019-53-2 loganic acid pentaacetate 
• 27856-66-2 secologanin tetraacetate 
• 71462-04-9 1,6-di-O-acetylloganol 
• 75-05-8 acetonitrile 
• 108-24-7 acetic anhydride 
• 76703-84-9 loganin tetraacetate 
• 18524-94-2 loganin 
• 19126-95-5 trimethylsilyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 82509-41-9 loganic acid 

Downstream Products

• 18524-94-2 loganin 
• 67596-51-4 loganoside 

Relevant articles and documents

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Iridoids from Symphoricarpos albus

Twelve compounds including secologanin, loganin, the aglycon of loganin, and a new iridoid called glucologanin were isolated from fruit of common snowberry Symphoricarpos albus (L.) Blake. The structure of glucologanin was confirmed using PMR and mass spe

Reductive, Radical-Induced Cyclizations of 5-Hexenals as a Biomimetic Model of the Chemistry of Secologanin Formation

A model reaction for studying the mechanism of the biological conversion of the iridoid loganin (1) to the secoiridoid secologanin (2) is the reductive, radical-induced cyclization of secologanin tetraacetate (4) to loganin tetraacetate.Treatment of 4 with Mg and Me3SiCl in THF at room temperature gives a mixture of the four possible C-6 and C-7 epimers of loganin tetraacetate in which the natural stereochemistry predominates.This result suggests that the biochemical event, which involves cleavage of the C-6 and C-7 bond of 1 in forming 2, may be a homolytic process that is initiated by formation of a carbon radical at C-8.The scope of the cyclization reaction, which formally occurred in a 5-hexanal moiety in 4, is defined by studies of the cyclization of six other δ,ε-unsaturated aldehydes.The results illustrate a new way for ring annulation through the reductive, radical-induced cyclization of δ,ε-unsaturated aldehydes.