1609192-27-9

Upstream product

• 100-39-0 benzyl bromide 
• 4773-96-0 mangiferin 
• 1609192-26-8 1,3,6-tri-O-benzyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-7-O-acetylxanthone 

Downstream Products

• 1609192-28-0 1,3,6-tri-O-benzyl-2-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)xanthone 

Relevant academic research and scientific papers

The new mangiferin chemical synthesis method and intermediate compound

The invention discloses a chemical semi-synthesis method of neomangiferin. The chemical semi-synthesis method comprises the following steps of sequentially carrying out acylation and protecting group conversion on mangiferin used as a starting material and selectively removing phenolacyl groups so as to obtain an intermediate compound represented by the formula D as shown in the description; carrying out glycosylation reaction by using bromotetraacyl glucose as a donor and a phase-transfer catalytic method to obtain an ntermediate compound represented by the formula E as shown in the description and finally removing acyl protecting groups under catalytic hydrogenation, or acid hydrolysis, or reduction and basic conditions to obtain neomangiferin, wherein the definitions of substituent groups in the formulas D and E are shown in the description. The chemical semi-synthesis method has the characteristics of mild reaction conditions, high yield, simplicity in operation, relatively low cost, high universality and like, is suitable for industrial mass production and has better application prospects.

Semi-synthesis of neomangiferin from mangiferin

Neomangiferin, a natural xanthone derivative bearing both O- and C-glucosides, was isolated from the leaves of Gentiana asclepiadea L. and has shown potential anti-diabetic activity. We describe herein the first semi-synthesis of neomangiferin from the natural C-glucoside mangiferin and glucose. The developed synthesis presents a facile protection strategy using Jurd's method to distinguish the different phenolic hydroxyl groups. Following this strategy, the regioselective protection of 1,3,6-hydroxyl groups was accomplished and neomangiferin was prepared by glycosylation under the phase-transfer catalysis conditions.