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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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its chemical synthesis has not been reported
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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

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Experimental program
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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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