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Chemosynthesis of glucuronide oleanane type double sugar chains triterpenoid saponin

A technology of aldoside oleanane and triterpene saponins, which is applied in the field of synthesis of oleanane-type pentacyclic triterpene saponins, and can solve problems such as limited synthesis reports

Inactive Publication Date: 2004-11-03
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its chemical synthesis has not been reported
In fact, the reports on the synthesis of other triterpene saponins are very limited so far.

Method used

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  • Chemosynthesis of glucuronide oleanane type double sugar chains triterpenoid saponin
  • Chemosynthesis of glucuronide oleanane type double sugar chains triterpenoid saponin
  • Chemosynthesis of glucuronide oleanane type double sugar chains triterpenoid saponin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of Ginsenoside Ro(1)

[0028] The synthetic route is shown in the figure below:

[0029]

[0030] Reagents and conditions: (a) K 2 CO 3 , Bu 4 NBr, CH 2 Cl 2 -H 2 O, reflux, 90%. (b) TBSOTf (0.1 equiv), CH 2 Cl 2 , 4 MS, rt, 91%.(c)Bu 3 P, THF-H 2 O, 75%. (d) TBSOTf (0.4 equiv), CH 2 Cl 2 , 4 Å MS, rt, 79%. (e) AcCl, MeOH-CH 2 Cl 2 , 0°C-rt, 89%. (f) TEMPO, Ca(ClO) 2 , KBr, Bu 4 NBr, CHCl 3 -H 2 O, 0°C, 89%. (g) NaOMe, MeOH-CH 2 Cl 2 , 72%.

[0031] Specific experiments and data:

[0032] (1) 2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranosyl oleanolic ester (4): oleanolic acid (195mg, 0.43mmol) and 2,3,4,6-tetra- O-Benzoyl-α-D-glucobromoside (377 mg, 1.3 equiv) was dissolved in CH 2 Cl 2 (5.0mL) and water (5.0.mL) two-phase system, and add K 2 CO 3 (151mg, 2.5 equivalents) and Bu 4 NBr (56 mg, 0.4 eq) was then heated to reflux until TLC showed the reaction was complete. The reaction system uses CH 2 Cl 2 Diluted, then...

Embodiment 2

[0040] Synthesis of GOTCAB Saponin 2

[0041] The synthetic route is shown in the figure below:

[0042]

[0043] Reagents and conditions: (a) TBSOTf (0.1 equiv), CH 2 Cl 2 , 4  MS, rt, 89%.(b) Bu 3 P, THF-H 2 O, 90%. (c) TBSOTf (0.4 equiv), CH 2 Cl 2 , 4 Å MS, rt, 90%. (d) AcCl, MeOH-CH 2 Cl 2 , 0°C-rt, 88%. (f) TEMPO, Ca(ClO) 2 , KBr, Bu 4 NBr, CHCl 3 -H 2 O, 0°C, 85%. (g) NaOMe, MeOH-CH 2 Cl 2 , 78%.

[0044] Specific experiments and data:

[0045] (1) 2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranoside-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 3)-4,6-di-O-acetyl-2-O-(2-azidomethyl)benzoyl-β-D-glucopyranosyl]oleanolic ester (13): the donor 12 (1.0g, 1.1 equivalents) and the acceptor Enzyme 4 (806 mg, 0.779 mmol) was dissolved in anhydrous CH 2 Cl 2 and add 4 Å molecular sieves. Under the protection of argon, TBSOTf (0.1 equivalent) was added dropwise to the system. After stirring at room temperature for 3 hours, the react...

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Abstract

The present invention provides practical GOTCAB saponin synthesis process. The synthesis process includes the following steps: connecting site-28 glucose chain; connecting site-3 glycosyl; connecting rest site-3 glycosyl after protecting radical operation; making site-6' hydroxy group empty via protecting radical operation; selectively oxidizing site-6' primer hydroxy group into carboxylic acid; and finally eliminating all the protecting radicals under alkali condition.

Description

technical field [0001] The invention relates to a synthesis method of oleanane type pentacyclic triterpene saponins, in particular to a synthesis method of glucuronide oleanane type disaccharide chain triterpene saponins. Background technique [0002] Glucuronide oleanane-type triterpene carboxylic acid 3,28-O-bisdesmoside (GOTCAB for short) is a type of saponin whose structure is shown in the figure below. Its characteristics are: (1) the aglycon is an oleane-type pentacyclic triterpene; (2) the 3-OH and 28-COOH of the triterpene are both substituted by sugar groups; (3) the 3-position sugar chain is β-D -Glucuronides are linked to aglycones. During 1962-1997, 192 GOTCAB saponins have been isolated and identified in 20 plant families [Tan, N.; Zhou, J.; Zhao, S. Phytochemistry 1999, 52, 153-192.]. Thereafter, new structures were discovered at an even faster rate. Some GOTCAB saponins have been found to have various biological and physiological activities. However, its c...

Claims

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Application Information

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IPC IPC(8): C07J63/00
Inventor 俞飚彭文杰林峰韩秀文
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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