Method for preparing stevioside

A technology of steviol glycoside and glycosidation reaction, which is applied in the field of stevioside preparation and can solve problems such as unreasonableness

Active Publication Date: 2018-12-18
JIANGXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The patent also mentions the use of TMSOTf strong Lewis acid catalysis at room temperature, wherein the protonated TfOH is a known super acid, its acidity far exceeds that of concentrated sulfuric acid with a concentration of 100%, which is also not possible for acid-sensitive substrates In addition, the patent also designs NIS to catalyze disaccharide glucosinolates. It is known that NIS is a good iodine reagent, and the substrate contains a terminal alkene, which is a kind of double bond with higher activity. bond, during our experiments, it was found that the double bond is easily iodized by NIS, so NIS catalysis is an extremely unwise choice for steviol glycoside substrates

Method used

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  • Method for preparing stevioside
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  • Method for preparing stevioside

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preparation example Construction

[0051] The preparation method of some compounds in the present invention is as follows:

[0052] 1. The preparation method of compound 9:

[0053]

[0054] We started from commercially available steviol, reacted with TBDPSCl under alkaline conditions, and obtained the receptor compound 9 required for our reaction through the conventional reaction conditions in this field.

[0055] 9: [α] D25 = -31.6 (c 1, CHCl3); 1H NMR (400MHz, CDCl3) δ7.69-7.66 (m, 4H), 7.45-7.40 (m, 2H), 7.38-7.34 (m, 4H ),2.93(d,J=4.8Hz,1H),2.78(d,J=4.8Hz,1H), 2.34(brs,1H),2.24-2.19(m,1H),2.14(dd,J=2.0, 11.2Hz, 1H), 1.35(dd, J=2.8, 11.2Hz, 1H), 1.27(s, 3H), 1.14(s, 9H), 0.76(s, 3H); 13C NMR(100MHz, CDCl3) δ176. 9,135.8 (2C),132.1(2C),130.1,127.7,74.9,65.4,57.1,53.9,48.8,46.7,45.8,45.2,41.7,41.5,40.8,39.5,38.6,34.8,29.3,27.3,22.3,19.7, 19.4, 19.3, 16.4, HRMS (ESI) calcd for C18H21IO8Na[M+Na]+595.3214, found 595.3210.

[0056] 2. The preparation method of compound 2-1:

[0057] Under nitrogen protect...

Embodiment 1

[0071] Embodiment 1: the preparation of Reb A

[0072]

[0073] Step (1): Compound 1 (110 mg, 0.064 mmol) was dissolved in CHCl 3 / H 2 O (4mL, v / v=1:1), add K at room temperature 2 CO 3 (26.4mg, 0.2mmol) and TBAB (41mg, 0.13mmol), stirred at room temperature for 10min, then added compound 2-1 (0.84mg, 0.13mmol) into the reaction system, reacted at 40°C for 14h, TLC detected that the reaction was complete , diluted with EA, washed three times with water, washed once with saturated sodium chloride, dried the organic phase with anhydrous sodium sulfate, filtered and suspended to dryness, column chromatography (PE / EA=1.5:1), the white foam compound 3-1 (125mg), Yield: 85%.

[0074] 3-1: [α] D 25 =+34.3(c 1,CHCl 3 ); 1 H NMR (400MHz, acetone-d 6 )δ8.16-8.11(m, 4H), 8.04-7.83(m, 17H), 7.64-7.28(m, 44H), 6.44(d, J=8.0Hz, 1H), 6.11(t, J=9.6Hz ,1H),6.05-5.99(m,2H),5.90(t,J=9.2Hz,1H),5.81(dd,J=8.0,10.0Hz,1H),5.76-5.66(m,4H),5.63( dd,J=7.6,9.6Hz,1H),5.52(d,J=8.0Hz,1H),5.40(...

Embodiment 2

[0091] Embodiment 2: the preparation of Reb D

[0092] The preparation of Reb D refers to the preparation of Reb A, the difference is that the sugar used is diglucoside 2-2, the reaction yield of step (1) is: 93%, the total of the two steps of step (2) and (3) Yield: 81%.

[0093] Reb D: [α] D 25 =-22.0(c 0.5, MeOH); 1 H NMR (400MHz, pyridine-d 5 )δ6.37(d, J=6.4Hz, 1H), 5.83(s, 2H), 5.69(s, 1H), 5.63(d, J=7.6Hz, 1H), 5.53(d, J=7.6Hz, 1H), 5.45(d, J=7.6Hz, 1H), 5.14(d, J=7.2Hz, 1H), 5.02(s, 1H), 4.64-3.89(m, 23H), 2.77(d, J=12.8 Hz,1H),2.54(d,J=11.2Hz,1H),2.28-1.68(m,13H),1.43(s,3H),1.16(s,3H), 1.01(d,J=12.0Hz,1H ),0.89(d,J=6.4Hz,1H),0.77(dd,J=10.4,14.4Hz,1H); 13 C NMR (100MHz, pyridine-d 5 )δ175.8, 154.0, 105.7, 104.8, 104.6, 104.5, 97.8, 93.6, 88.1, 86.6, 81.0, 80.8, 79.0, 78.6, 78.4 (2C), 78.2, 78.1, 78.0, 77.4, 76.4, 76.2, 75.3, 72. 72.0, 71.6, 70.8, 69.9, 63.2, 63.0, 62.3(2C), 62.1, 57.4, 53.9, 49.7, 47.6, 44.3, 44.1, 42.2, 41.8, 40.6, 39.7, 37.8, 29.2, 22.2, 20.5...

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Abstract

The invention provides a convergent stevioside preparing method. The method comprises the following steps: a stevioside receptor, base and a phase transfer catalyst are dissolved in a solvent, and arereacted at room temperature for 5 to 60 minutes, a glycosyl donor 2 is added, a reaction is carried out at 40 to 60 DEG C for 10 to 18 hours, a glycosidation product is obtained with a yield being 80to 85%, and a protecting group is removed to obtain high-purity compounds Red A, Red D and Red M. The method provides a succinctly implementable strategy to facilitate the large acquisition of stevioside, especially stevioside with low content.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and more specifically relates to a preparation method of steviol glycosides. Background technique [0002] Stevioside is a kaurane-type diterpene disaccharide chain glycoside mixture extracted from the leaves of Stevia rebaudiana Bertoni. Its sweetness is 150-300 times that of sucrose, and it is a strong sweetener. Compared with other sweeteners, it has low cost of use (compared with sucrose, which can reduce the cost by more than 60%), stable properties (high temperature and acid-base resistance), and high safety in use (long-term toxicology and pharmacological studies have shown that the main component of steviol glycosides It does not participate in metabolism in the body, does not accumulate, has no toxicity and genetic hazards, and does not cause changes in blood sugar and insulin levels after ingestion, so it is also suitable for diabetic patients. Its safety has passed the US Food and Drug...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/256C07H1/00
CPCC07H1/00C07H15/256Y02P20/55
Inventor 孙建松乔治刘慧廖进喜
Owner JIANGXI NORMAL UNIV
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