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Method for synthesizing primary monohydroxytrimethylsilyl disaccharide

A primary monohydroxy trimethylsilyl disaccharide, trimethylsilyl technology, applied in the field of chemical synthesis, can solve the problems of difficult control of obtaining target products, difficult control of reactions, corrosion of equipment, etc. By-products, the effect of avoiding neutralization reactions

Inactive Publication Date: 2015-04-01
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing technology still requires low temperature (0-4°C), and the target product is not easy to control during the reaction; in large-scale reactions, refrigeration auxiliary equipment and corrosion-resistant equipment are required, and the conditions are relatively harsh
[0004] In the previous reaction to remove TMS groups, acid or alkali was often used as a catalyst. The reaction was not easy to control and would corrode the equipment. After the reaction, neutralization, desalination and other post-treatments were troublesome.

Method used

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  • Method for synthesizing primary monohydroxytrimethylsilyl disaccharide
  • Method for synthesizing primary monohydroxytrimethylsilyl disaccharide
  • Method for synthesizing primary monohydroxytrimethylsilyl disaccharide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 2,3,4,2',3',4',6'-seven- O - Trimethylsilyl-D-cellobiose

[0024] 2,3,4,6,2',3',4',6'-eight- O -Trimethylsilyl-D-cellobiose (113mg, 0.12mmol) and ammonium acetate (76mg, 0.96mmol), dissolved in dichloromethane / methanol solution (2.3mL / 2.3 mL), reacted at room temperature for 10h. After the reaction, rotary evaporation, column chromatography (petroleum ether / ethyl acetate = 10 / 1), 2,3,4,2',3',4',6'-hepta- O - Trimethylsilyl-D-cellobiose (56 mg, 54.9 %), the structure of which is figure 1 shown.

[0025] 1 H NMR (400 MHz, CDCl 3 ) δ 4.44 (d, J = 7.4 Hz, 1H), 4.36 (d, J = 7.7 Hz, 1H), 3.89 (d, J = 10.9 Hz, 1H), 3.82–3.70 (m, 2H), 3.63 (s, 1H), 3.50 (t, J = 11.7 Hz, 1H), 3.41 (t, J = 8.9 Hz, 1H), 3.37 (d, J = 8.7 Hz, 1H), 3.23 (d, J = 7.7 Hz, 5H), 0.20 – 0.07 (m, 63H).

[0026] 13 C NMR (101 MHz, CDCl3) δ 102.67, 98.66, 78.26, 78.03, 76.60, 76.50 76.48, 75.97, 75.08, 72.99, 63.47, 60.90, 4.10, 1.72, 1.62, 1.58, 1.43, 0.92, 0.05.

[0027] ESI-MS. ...

Embodiment 2

[0029] 2,3,4,2',3',4',6'-seven- O -Trimethylsilyl-D-lactose

[0030] 2,3,4,6,2',3',4',6-eight- O -Trimethylsilyl-D-lactose (157mg, 0.17mmol) and ammonium acetate (104mg, 1.36mmol), dissolved in dichloromethane / methanol solution (3.2mL / 3.2 mL), reacted at room temperature for 3h. After the reaction, rotary evaporation, column chromatography (petroleum ether / ethyl acetate = 10 / 1), 2,3,4,2',3',4',6'-hepta- O - Trimethylsilyl-D-lactose (66 mg, 45.8 %), the structure of which is figure 2 shown.

[0031] 1 H NMR (400 MHz, CDCl 3 ) δ 5.02 (d, J = 3.1 Hz, 1H), 4.28 (t, J = 8.7 Hz, 1H), 4.00 (dd, J = 11.1, 2.6 Hz, 1H), 3.83 (dt, J = 17.4, 8.7 Hz, 1H), 3.73 (q, J = 8.6 Hz, 2H), 3.70 – 3.56 (m, 4H), 3.50 (dd, J = 11.1, 3.7 Hz, 1H), 3.44 – 3.29 (m, 3H), 0.17 – 0.06 (m, 63H).

[0032] 13 C NMR (101 MHz, CDCl 3 ) δ 102.47, 94.19, 75.82, 75.65, 74.90, 74.01, 72.43, 72.24, 71.85, 71.15, 62.53, 60.73, 0.91, 0.83, 0.69, 0.51, 0.47, 0.29, 0.02.

[0033] ESI-MS. Anal. C...

Embodiment 3

[0035] 2,3,4,2',3',4',6'-seven- O -Trimethylsilyl-α,α-Trehalose

[0036] 2,3,4,6,2',3',4',6'-eight- O -Trimethylsilyl-α,α-trehalose (150mg, 0.16mmol) and ammonium acetate (99mg, 1.28mmol), dissolved in dichloromethane / acetone solution (3.0mL / 3.0 mL), reacted at room temperature for 10h. After the reaction, rotary evaporation, column chromatography (petroleum ether / ethyl acetate = 10 / 1), 2,3,4,2',3',4',6'-hepta- O -Trimethylsilyl-α,α-trehalose (40mg, 30%), the structure of which is image 3 shown.

[0037] 1 H NMR (400 MHz, CDCl 3 ) δ 4.92 (d, J = 3.1 Hz, 1H), 4.87 (d, J = 3.1 Hz, 1H), 3.90 – 3.83 (m, 2H), 3.82 (d, J = 9.5 Hz, 1H), 3.80 – 3.73 (m, 1H), 3.70 – 3.60 (m, 4H), 3.47 – 3.41 (m, 1H), 3.41 – 3.34 (m, 3H), 0.15 – 0.07 (m, 63H ).

[0038] 13 C NMR (101 MHz, CDCl 3 ) δ 94.90, 94.73, 73.95, 73.88, 73.86, 73.27, 73.23, 73.20, 72.20, 71.94, 62.61, 62.19, 1.52, 1.48, 1.41, 1.33, 0.58, 0.56, 0.17.

[0039] ESI-MS. Anal. Calcd for C 33 h 78 o 11 Si 7 N...

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Abstract

The invention discloses a method for synthesizing primary monohydroxytrimethylsilyl disaccharide and belongs to the technical field of chemical synthesis. The process comprises the following steps: taking ammonium acetate as a selective removal agent of trimethylsilyl at room temperature, taking a disaccharide subjected to full trimethylsilyl protection as a substrate, stirring and reacting in an organic solvent, selectively removing one trimethylsilyl at the primary position of the disaccharide, thereby obtaining the primary monohydroxytrimethylsilyl disaccharide. The method disclosed by the invention is mild in reaction conditions, high in region selectivity and high in yield and is applied to scientific research and development and large-scale production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to the regioselective reaction of carbohydrates, that is, to use the regioselective reaction as a substrate to synthesize the primary monohydroxytrimethylsilyl disaccharide in one step. 2,3,4,2',3',4',6'-Hepta-O-trimethylsilyl disaccharide derivatives. Background technique [0002] Carbohydrates, together with nucleic acids and proteins, are called the three important living substances, and play a key role in signal transduction and biological recognition in living organisms. The chemical synthesis of sugars is of great significance. The simulated synthesis of physiologically active oligosaccharides can not only verify the important conclusions about the structure and biological functions of natural oligosaccharides, but also further chemically modify them, change their structures, and study their mechanism of action. It can create conditions for the synthesis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H23/00C07H1/00
Inventor 崔艳丽许珊珊毛旸易毛建卫
Owner ZHEJIANG UNIV