2-nitroglycal and efficient synthesis method thereof

Abstract

The invention discloses an efficient synthesis method of 2-nitroglycal, and belongs to the technical field of synthesis of sugar. The structure of the 2-nitroglycal is shown in the specification. Secondly, the invention also provides a preparation method of the 2-nitro saccharide alkene, and the preparation method provided by the invention can be used for efficiently preparing the 2-nitroglycal through one-step synthesis.

Description

technical field [0001] The invention belongs to the field of sugar synthesis, and in particular relates to 2-nitrosugarene and a high-efficiency synthesis method thereof. Background technique [0002] 2-Nitrosugars are important intermediates in sugar chemistry. This is due to the presence of conjugated nitroalkenes and enol ether moieties, which open up many possibilities for synthetic manipulations. For example, this combination makes these substrates useful for Michael addition reactions, Diels-Alder reactions, (2+3) cycloaddition reactions, etc. In addition, nitro groups can be converted into many other useful functional groups, such as carbonyl and amino groups. 2-Nitrosugar has been used as an excellent glycosyl donor in glycoprotein synthesis to synthesize glycoproteins, glycosylamino acids and glycoproteins. They are also used in the synthesis of biheterocyclic molecules such as fused heterocycles, carbon glycosides, two-carbon branched sugars, etc. [0003] Aimi...

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Problems solved by technology

[0003] Aiming at the synthesis of the 4- and 6-position silicon fork protection and the 3-position benzyl protection of the target molecular Proteus sugar antigen, the inventors initially used -40°C HNO 3 -Ac 2 Acetyl nitrate generated by O reacts with glucosene, and then eliminates 2-nitroglucosene under the condition of triethylamine at 0°C; Vankar is based on the combination of acetyl chloride and silver nitrate as the source of nitronium ions and the improved TBAN- Trifluoroacetic anhydride (TFAA)-Et 3 Unfortunately, the N system did not obtain the desired nitrosugarene product

Analyzing the reason for its failure, it is guessed that it is due to the reason of the silicon-based protecting group, which has a large steric hindrance and strong electron donating ability, so it cannot be successfully eliminated into a normal product.

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