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Method for regioselectively removing O-benzyl protective group of sugar

A technology of benzyl and alkyl groups, applied in the field of regioselective removal of sugar O-benzyl protecting groups, can solve problems such as limiting the development and utilization of natural oligosaccharides

Inactive Publication Date: 2010-07-14
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This situation greatly limits the further development and utilization of such abundant natural oligosaccharides.

Method used

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  • Method for regioselectively removing O-benzyl protective group of sugar
  • Method for regioselectively removing O-benzyl protective group of sugar
  • Method for regioselectively removing O-benzyl protective group of sugar

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Preparation of methyl 2,3,4-tri-O-benzyl-triethylsilyl-α-D-mannanose (Method 1)

[0079] Under the protection of CO gas, 3.19mL (20mmol) Et 3 SiH is added to 35mg (0.1mmol) Co 2 (CO) 8 In, stirring at room temperature for 30 minutes. Then, 6 mL of anhydrous benzene was added to 554 mg (1 mmol) of methyl 2,3,4,6-tetra-O-benzyl-α-D-mannanose, and added to the above reaction solution after deoxygenation. Then it was transferred to the autoclave and reacted at 90 atm CO and 90°C for about 48 hours. After the reaction, the reaction solution was transferred to a round-bottomed flask, 0.1 mL of pyridine was added, and air was vented for about 20 minutes, and then passed through a silica gel column of about 5 cm, and then separated by a pressurized column (petroleum ether / ethyl acetate = 15: 1) Get 520 mg of colorless syrup. The yield was 90%. 1 H NMR(400MHz, C 6 D 6 )δ7.00-7.09(m, 6H), 6.77-6.90(m, 11H), 4.75(d, 1H, J=11.4Hz, -CH 2 Ph), 4.46 (d, 1H, J = 1.3 Hz, H-1), 4.42 (d, 1...

Embodiment 2

[0083] Preparation of methyl 2,3,4-tri-O-benzyl-triethylsilyl-α-D-galactopyranose

[0084] Under the protection of CO gas, 3.19mL (20mmol) Et 3 SiH is added to 35mg (0.1mmol) Co 2 (CO) 8 In, stirring at room temperature for 30 minutes. Then, 6 mL of anhydrous benzene was added to 554 mg (1 mmol) of methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranose, and added to the above reaction solution after deoxygenation. Then it was transferred to the autoclave and reacted at 90 atm CO and 90°C for about 48 hours. After the reaction, the reaction solution was transferred to a round-bottomed flask, 0.1 mL of pyridine was added, and air was vented for about 20 minutes, and then passed through a silica gel column of about 5 cm, and then separated by a pressurized column (petroleum ether / ethyl acetate = 15: 1) 491 mg of colorless syrup is obtained. The yield was 85%. 1 H NMR(400MHz, C 6 D 6 )δ7.15-7.18(m, 2H), 7.01-7.05(m, 4H), 6.76-6.92(m, 10H), 4.88(d, 1H, J=11.3Hz, -CH 2 Ph), 4.52 (d, 1H, J...

Embodiment 3

[0086] Preparation of methyl 2,3,4-tri-O-benzyl-triethylsilyl-α-D-glucopyranose

[0087] Under the protection of CO gas, 3.19mL (20mmol) Et 3 SiH is added to 35mg (0.1mmol) Co 2 (CO) 8 In, stirring at room temperature for 30 minutes. Then, 6 mL of anhydrous benzene was added to 554 mg (1 mmol) of methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose, and added to the above reaction solution after deoxygenation. Then it was transferred to the autoclave and reacted at 90 atm CO and 90°C for about 48 hours. After the reaction, the reaction solution was transferred to a round-bottomed flask, 0.1 mL of pyridine was added, and air was vented for about 20 minutes, and then passed through a silica gel column of about 5 cm, and then separated by a pressurized column (petroleum ether / ethyl acetate = 15: 1) 462 mg of colorless syrup is obtained. The yield was 80%. 1 H NMR(400MHz, C 6 D 6 )δ7.05 (d, 4H, J = 7.8 Hz), 6.99 (d, 2H, J = 7.2 Hz), 6.77 690 (m, 10H), 4.76 (d, 1H, J = 11.4H, -CH 2 Ph), ...

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Abstract

The invention discloses a novel method for regioselectively removing O-benzyl protective group of sugar. The reaction conditions are mild and the selectivity is high. Moreover, the invention additionally provides formula (IV) intermediate compound. Definitions of substituent groups are detailed in an instruction book.

Description

Technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for regioselectively removing sugar O-benzyl protective groups Background technique [0002] In sugar chemistry, because sugars have multiple hydroxyl groups, the selective protection and deprotection of hydroxyl groups is very important, especially in the multi-step synthesis of complex oligosaccharides. Because of its easy formation, stable properties and a variety of removal methods to choose from, benzyl ether has become one of the most widely used hydroxyl protecting groups. [0003] Various methods for the regioselective introduction of benzyl ethers, including selective benzylation on the sugar ring and regioselective ring opening of benzylidene acetals, have been developed. One of the attractive strategies is to perform regioselective debenzylation of readily available fully benzylated glycosyl precursors to achieve selective benzylic protection of carbohydrates. Met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H15/18C07H1/00
CPCY02P20/55
Inventor 李中军尹昭军孟祥豹李阳冰王博李庆李树春
Owner PEKING UNIV
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