20586-11-2

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

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

Relevant academic research and scientific papers

7-O-Acetyl loganic acid from Alangium platanifolium var. Trilobum

7-O-Acetyl loganic acid was isolated for the first time in Nature from the stem bark of Alangium platanifolium var. trilobum.

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

Iridoids, XXII. - Glucosidation of Hemiacetals. - Highly Stereoselective Synthesis of Iridoid Glucosides

Reaction of the racemic iridoid aglucone acetates 9d-12d with the trimethylsilyl β-glucopyranoside 4a in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate (7) in acetonitrile or liquid sulfur dioxide at -30 deg C and -50 deg C, respectively, followed by solvolysis gives in excellent yields nearly exclusively the β-glucosides 9g and 11g.Glucosidation of the enantiomerically pure acetates 9d/10d affords the β-glucoside 9g.In a similar way, the biosynthetical key intermediate loganin (1) is obtained from 16a in 60 percent yield.

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.

IRIDOID GLUCOSIDES FROM CAMPSIS CHINENSIS

Two new iridoid glucosides, 5-hydroxycampenoside and cachineside I, were isolated together with tecomoside from leaves of Campsis chinensis and their structures were elucidated.The absolute stereochemistry of 5-hydroxycampenoside has been established by X-ray analysis, and the structural correlation between 5-hydroxycampenoside and tecomoside has been determined by spectral and chemical experiments. - Key Word Index: Campsis chinensis; Bignoniaceae; iridoid glucosides; 5-hydroxycampenoside; tecomoside; cachineside I; X-ray structure.

245. Studies on Monoterpene Glucosides and Related Natural Products. Part 51. Absolute Structures of Hydrangenosides A, B, C, D, E, F, and G. Novel Type Secoiridoid Glucosides from Two Hydrangea Plants

From Hydrangea macrophylla var. macrophylla, four new secoiridoid glucosides, hydrangenosides A, B, C and D, were isolated, along with the known iridoid glucosides loganin, secologanin, secologanic acid and sweroside.Moreover, hydrangenosides E, F, and G,

NEW IRIDOID GLUCOSIDES, CAMPENOSIDE AND 5-HYDROXYCAMPENOSIDE, FROM CAMPSIS CHINENSIS VOSS

Two novel iridoid glucosides, campenoside and 5-hydroxycampenoside were isolated from the leaves of Campsis chinensis Voss and their structures were shown to be 2 and 3, respectively.